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

HRID 2099293노트

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HRID 2099293 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-66afa5da8e76452dae12883c50c56b42
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569579B2

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