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

HRID 443462

반응식

HRID 443462 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7b1af7eda4f94ac9be4d8e4ce7aeb94e
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04260633

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