m-Chlorophenylacetonitrile → (4S)-2-(3-chlorophenyl)-4-hydroxy-6-[(phenylmethyl)oxy]hexanenitrile

HRID 2099293ノート

反応式

HRID 2099293 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[C:16]1([CH2:22][O:23][CH2:24][CH2:25][C@@H:26]2[CH2:28][O:27]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:28][C@H:26]([OH:27])[CH2:25][CH2:24][O:23][CH2:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 73722m-ChlorophenylacetonitrileHCID 11789783(2R)-2-[2-(Phenylmethoxy)ethyl]oxiraneHCID 178418339Butyllithium

生成物 1

HCID 57794819(4S)-2-(3-chlorophenyl)-4-hydroxy-6-[(phenylmethyl)oxy]hexanenitrile収率 59.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

(3-Chlorophenyl)acetonitrile (8.62 mL, 72.9 mmol) in 100 ml of THF was cooled to −78° C. Butyllithium (35.1 mL, 56.1 mmol, 1.6 M in THF) was added over 20 minutes and stirred for an additional 15 min at −78° C. (2R)-2-{2-[(phenylmethyl)oxy]ethyl}oxirane (10.0 g, 56.1 mmol, Synthesis 1992, 7, 621-623) in 20 mL of THF was added over 30 minutes and stirred for an additional hour at −78° C. After warming to room temperature the solvent was evaporated and the orange red oil was chromatographed on silica gel with 20-25% EtOAc in Hexanes to give the title compound (11.05 g, 58%). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.8 (m, 3H) 3.6 (m, 1H) 3.7 (m, 2H) 4.1 (m, 2H) 4.5 (m, 2H) 7.3 (m, 9H).

後処理

  1. additionwas added over 30 minutes
  2. temperatureAfter warming to room temperature the solvent
  3. customwas evaporated
  4. customthe orange red oil was chromatographed on silica gel with 20-25% EtOAc in Hexanes

出典と根拠

ORDレコード
ord-66afa5da8e76452dae12883c50c56b42
出典データセット
uspto-grants-2009_08
特許番号
US07569579B2

反応ノート

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