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

HRID 443462

反応式

HRID 443462 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7b1af7eda4f94ac9be4d8e4ce7aeb94e
出典データセット
uspto-grants-1981_04
特許番号
US04260633

関連ノート

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