Water → (2S)-2-((1-Naphthalenyloxy)methyl)oxirane

HRID 1107051

反応式

HRID 1107051 の反応式
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F-].[Cs+].[N+](C1C=C(S(O[CH2:27][C@H:28]2[O:30][CH2:29]2)(=O)=O)C=CC=1)([O-])=O.O>CN(C=O)C>[O:30]1[CH2:29][C@H:28]1[CH2:27][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 962WaterHCID 70051-NaphtholHCID 25953Cesium fluorideHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

生成物 1

HCID 148933(2S)-2-((1-Naphthalenyloxy)methyl)oxirane収率 96.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

1-Naphthol (1.0 g) was dissolved in DMF (8 ml) under nitrogen atmosphere and the solution was cooled to 0° C. 25 Cesium fluoride (2.1 g) was added thereto and the mixture was stirred for 1 hour. Then, (S)-glycidyl m-nitrobenzenesulfonate (1.80 g, 99.3% e.e.) was added thereto and the mixture was stirred for 24 hours at the same temperature. After the reaction water was added to the mixture, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/ethyl acetate; 6:1) to give 1.34 g of (S)-1-(2,3-epoxypropoxy)naphthalene (yield 96.5%, optical purity 99.2% e.e.) as a colorless oil.

後処理

  1. stirringthe mixture was stirred for 24 hours at the same temperature
  2. additionwas added to the mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate, condensed

出典と根拠

ORDレコード
ord-a0d145534f774bbab6d2e72ab5b3b57f
出典データセット
uspto-grants-2000_05
特許番号
US06057476

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