Acetone Cyanohydrin → (3S)-3-hydroxy-3-phenylpropanenitrile
Reaction equation
[CH2:1]1[O:9][C@@H:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(C)(O)[C:12]#[N:13].C(N(CC)CC)C>O1CCCC1>[C:3]1([C@@H:2]([OH:9])[CH2:1][C:12]#[N:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 40.0 g of (R)-styrene oxide, 31.12 g of acetone cyanohydrin, 36.96 g of triethylamine, and 150 ml of tetrahydrofuran was heated at reflux for 18 hours. The reaction mixture was cooled, concentrated in vacuo, diluted with 200 ml of 2N potassium hydroxide, and extracted with diethyl ether. The ether extracts were combined, dried over magnesium sulfate, and concentrated in vacuo providing 34.3 g of the title intermediate.
Workup
- temperaturewas heated
- temperatureat reflux for 18 hours
- temperatureThe reaction mixture was cooled
- concentrationconcentrated in vacuo
- additiondiluted with 200 ml of 2N potassium hydroxide
- extractionextracted with diethyl ether
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-031d64a9ec0c47989fe335f90f58eb3c
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05136078
Reaction notes
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