Diethyl Ether → (r/s)-3-Cyclohexyl-2-hydroxy-propanoic acid, 4-(methoxy)benzyl ester

HRID 1386682ノート

反応式

HRID 1386682 の反応式
CO[C:3]1[CH:14]=[CH:13][C:6]([CH2:7][C:8](=[O:12])[C:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[CH:15]1([CH2:21][Mg]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.BrCC1CCCCC1.BrCCBr.C[CH2:37][O:38]CC>C1(C)C=CC=CC=1>[CH:6]1([CH2:7][CH:8]([OH:12])[C:9]([O:11][CH2:21][C:15]2[CH:20]=[CH:19][C:18]([O:38][CH3:37])=[CH:17][CH:16]=2)=[O:10])[CH2:5][CH2:4][CH2:3][CH2:14][CH2:13]1

参加物

7

反応物 5

HCID 3283Diethyl EtherHCID 78391,2-DibromoethaneHCID 137636Cyclohexane, (bromomethyl)-HCID 19878614-(Methoxy)benzylglyoxylateHCID 178419664HCID 178419664、化合物

生成物 1

HCID 76635352(r/s)-3-Cyclohexyl-2-hydroxy-propanoic acid, 4-(methoxy)benzyl ester収率 26%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 0.50 g (2.32 mmol) of 4-(methoxy)benzylglyoxylate (azeotropically dried with 2×25 mL of toluene) in 2 mL of ether at −78° C. was treated with 7 mL of 0.5 M of cyclohexylmethylmagnesium bromide (prepared from 1.0 mL (7.1 mmol) of bromomethylcyclohexane, 174 mg (7.1 mmol) of Mg, 0.1 mL (1.1 mmol) of 1,2-dibromoethane in 14 mL of ether) and the resulting mixture was stirred cold for 1 h. The reaction was quenched with 1 N NaHCO3 and the quenched mixture was partitioned between 100 mL of ether and 100 mL of sat'd NaHCO3. The aqueous layer was separated and extracted with 100 mL of ether. The combined organic layers were dried over MgSO4 and concentrated. Flash chromatography on silica gel using 4:1 v/v hexanes/EtOAc afforded 180 mg (26%) of the title compound: RF: 0.32 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 0.84-1.82 (m, 13H), 3.81 (s, 3H), 4.23 (m, 1H), 5.14 (s, 2H), 6.90 (d, J=8.7, 2H), 7.29 (d, J=8.7, 2H).

後処理

  1. customThe reaction was quenched with 1 N NaHCO3
  2. customthe quenched mixture was partitioned between 100 mL of ether and 100 mL of sat'd NaHCO3
  3. customThe aqueous layer was separated
  4. extractionextracted with 100 mL of ether
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-1e05096631594779aeed257b97c17257
出典データセット
uspto-grants-2001_07
特許番号
US06265434B1

反応ノート

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