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

HRID 443462

Reaction equation

HRID 443462 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-7b1af7eda4f94ac9be4d8e4ce7aeb94e
Source dataset
uspto-grants-1981_04
Patent number
US04260633

Linked notes

Loading…