Acetone Cyanohydrin → 5-[2-(Phenylmethoxy)ethyl]furan-2-propanenitrile
Reaction equation
CCO[C:4](/[N:6]=N/C(OCC)=O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[CH2:33][CH2:34][C:35]1[O:36][C:37]([CH2:40][CH2:41][O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:38][CH:39]=1.CC(C)(O)C#N>C1COCC1>[C:44]1([CH2:43][O:42][CH2:41][CH2:40][C:37]2[O:36][C:35]([CH2:34][CH2:33][C:4]#[N:6])=[CH:39][CH:38]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
DEAD (1.285 mL, 8.17 mmol) was added to a stirred solution of Ph3P (2.14 g, 8.17 mmol) in 12 mL of dry THF at 0° C. The solution was stirred for 30 min at rt and compound 255E (670 mg, 2.72 mmol) was added. The reaction was stirred for 15 min and acetone cyanohydrin (0.745 mL, 8.17 mmol) was added at −15° C. The reaction was stirred for 30 min at −15° C., then at rt overnight. The mixture was then concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 100% CH2Cl2 gave 180 mg (0.705 mmol, 26%) of compound 255F as a colorless oil.
Workup
- stirringThe reaction was stirred for 15 min
- stirringThe reaction was stirred for 30 min at −15° C.
- customat rt
- customovernight
- concentrationThe mixture was then concentrated under reduced pressure
- customPurification by flash chromatography on silica gel eluting with 100% CH2Cl2
Sources & evidence
- ORD record
- ord-71998fdbac7a4a2a9783924b547e9072
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07655689B2
Reaction notes
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