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US4361702A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of trans-3-formylbut-2-enenitrile

Assignee: Alberta Innovates
•
Filing: 1980-01-21
•
Granted: 1982-11-30
•
Expires: 2000-01-21
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Abstract

Abstract A process is provided for the preparation of trans-3-formylbut-2-enenitrile (V), a key intermediate in the synthetic pathway leading to trans-zeatin (I) and dihydrozeatin (II), both of which are naturally occurring cytokinins. The process involves a base catalyzed condensation of a dialkyl or cyclic acetal of pyruvaldehyde (III) with acetonitrile to yield the corresponding dialkyl or cyclic acetal of 3-formylbut-2-enenitrile (IV). The reaction proceeds regioselectively to form the favored trans-isomer in good yield. The alpha , beta -unsaturated nitrile thus formed is hydrolyzed under acidic conditions to yield trans-3-formylbut-2-enenitrile (V), which can be easily distilled without contamination of the cis-isomer. The trans-3-formylbut-2-enenitrile can be selectively or exhaustively reduced to form either trans-3-hydroxymethylbut-2-enylamine (VI) or 3-hydroxymethylbutylamine (VII), which compounds can be condensed with 6-chloropurine (IX) by known methods to form trans-zeatin or dihydrozeatin respectively.

Inventors

  • 👤 Shi-Chow Chen
  • 👤 John M. MacTaggart

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 22:52
CPC Classifications
C; C07; C07C; C07C255/00; C07D; C07D319/00; C07D319/04; C07D319/06

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 68 words
The process comprising: reacting a pyruvaldehyde acetal having the general formula ##STR8## where R is an alkyl, cyloalkyl, substituted alkyl, or alkenyl group having from about 1-10 carbon atoms, or part of a methylene chain in a cyclic acetal of a 5-10 membered ring structure, with acetonitrile in the presence of a strong base at an elevated temperature for a time sufficient to form an acetal of 3-formylbut-2-enenitrile.
Claim 2
Dependent Claim 68 words
The process comprising: reacting a pyruvaldehyde acetal having the general formula ##STR8## where R is an alkyl, cyloalkyl, substituted alkyl, or alkenyl group having from about 1-10 carbon atoms, or part of a methylene chain in a cyclic acetal of a 5-10 membered ring structure, with acetonitrile in the presence of a strong base at an elevated temperature for a time sufficient to form an acetal of 3-formylbut-2-enenitrile.
Claim 3
Dependent Claim 16 words
The process as set forth in claim 1 wherein: the pyruvaldehyde acetal is a pyruvaldehyde dialkylacetal.
Claim 4
Dependent Claim 15 words
The process as set forth in claim 1 wherein: the pyruvaldehyde acetal is pyruvaldehyde dimethylacetal.
Claim 5
Dependent Claim 15 words
The process as set forth in claim 1 wherein: the pyruvaldehyde acetal is pyruvaldehyde diethylacetal.
Claim 6
Dependent Claim 15 words
The process as set forth in claim 1 wherein: the pyruvaldehyde acetal is pyruvaldehyde diisopropylacetal.
Claim 7
Dependent Claim 14 words
The process as set forth in claim 1 wherein: the pyruvaldehyde acetal is 2-acetyl-1,3-dioxacycloalkane.
Claim 8
Dependent Claim 14 words
The process as set forth in claim 1 wherein: the pyruvaldehyde acetal is 2-acetyl-1,3-dioxan.
Claim 9
Dependent Claim 37 words
The process as set forth in claim 1 wherein the base is selected from the group consisting of an alkali alkoxide, sodium hydroxide, potassium hydroxide; and the reaction is carried out in excess acetonitrile at reflux temperature.

References Cited (Backward Citations)

US3833637A Cited
US3960923A Cited
US4156690A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-11-29 1986-05-31 1986-11-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-11-29 1990-05-31 1990-11-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-11-29 1994-05-31 1994-11-30 $7700.00 Window Closed / Lapsed

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