Triethylamine → (2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

HRID 1680799Notes

Reaction equation

HRID 1680799 reaction equation
C1([C@H](NC(=O)[O:15][C@H:16]([C:30]#[N:31])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:18]=2)C)C2C(=CC=CC=2)C=CC=1.C(N(CC)CC)C.Cl[SiH](Cl)Cl>C1C=CC=CC=1>[C:30]([C@@H:16]([OH:15])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:18]=1)#[N:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24811TrichlorosilaneHCID 54266452(S)-alpha-cyano-3-phenoxybenzyl (R)-N-1-(1-naphthyl)ethylcarbamate

Product 1

HCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.91 g (6.99 mmol) of (S)-α-cyano-3-phenoxybenzyl (R)-N-1-(1-naphthyl)ethylcarbamate in 30 ml of dry benzene under a nitrogen atmosphere is added 1.07 ml (0.78 g, 7.7 mmol) of triethylamine followed immediately by 0.75 ml (1.0 g, 7.4 mmol) of trichlorosilane. The reaction is heated at 50° for 3 hours and is then worked up and purified following the procedure of Example 4. The more polar band on the tlc plate is removed and extracted with trichloromethane to yield (S)-α-cyano-3-phenoxybenzyl alcohol, specific rotation [α]D25 =-14.6° (c=11 mg/ml in acetone).

Workup

  1. temperatureThe reaction is heated at 50° for 3 hours
  2. custompurified
  3. customThe more polar band on the tlc plate is removed
  4. extractionextracted with trichloromethane

Sources & evidence

ORD record
ord-51d659225e9e4d0785c2c585432d1f69
Source dataset
uspto-grants-1981_06
Patent number
US04276230

Reaction notes

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