Acetic Acid → 4-Cyano-tetrahydro thiophene-3-carboxylic acid methyl ester
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
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
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-d3cf14a7469c4dbfa5115cc78f7159d4
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07176241B2
Reaction notes
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