Acetic Acid → 4-Cyano-tetrahydro thiophene-3-carboxylic acid methyl ester

HRID 30198

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[C:9](=O)[CH2:8][S:7][CH2:6]1)=[O:4].[C-:11]#[N:12].[K+].C(O)(=O)C.OP(O)(O)=O>CO.O.[Cl-].[Na+].O>[CH3:1][O:2][C:3]([CH:5]1[CH:9]([C:11]#[N:12])[CH2:8][S:7][CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-oxotetrahydro thiophene-3-carboxylic acid methyl ester (4 g, 25 mmol) in methanol (7 ml), cooled at 0° C., a solution of potassium cyanide (1.68 g, 30 mmol) in water (10 ml) was added. The mixture was acidified with acetic acid (1.5 ml, 25 mmol) and stirred at 0° C. for 8 hours. Then the mixture was acidified with H3PO4 and diluted with brine (50 ml) and extracted with CH2Cl2 (4×30 ml). The organic layers were dried over sodium sulfate and concentrated to give 4-cyano-tetrahydro thiophene-3-carboxylic acid methyl ester in 75% yield.

Workup

extractionextracted with CH2Cl2 (4×30 ml)
dry with materialThe organic layers were dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-c127cb7733094ef09bbaf4730a2d36ae
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423057B2

Linked notes

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