Methanol → (1R)-1-(2-chlorophenyl)ethan-1-ol

HRID 2092445ノート

反応式

HRID 2092445 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.CSC.B.CO>C1COCC1.O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([OH:10])[CH3:9]

参加物

8

反応物 4

HCID 887MethanolHCID 72864Ethanone, 1-(2-chlorophenyl)-HCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 12423031(Dimethyl sulfide)trihydroboron

生成物 1

HCID 6999092(1R)-1-(2-chlorophenyl)ethan-1-ol

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2′-Chloroacetophenone (8.4 mL, 65 mmol) and (S)-(−)-2-methyl-CBS-oxazaborolidine (0.90 g, 0.32 mmol) were combined in THF (75 mL). Borane methyl sulfide complex (2M in THF; 21.5 mL, 43 mmol) was added over 20 minutes, and the reaction was stirred at room temperature for 30 minutes. MeOH was added, and the mixture was worked-up with CH2Cl2 and H2O. The organic layer was concentrated to give the title compound.

後処理

  1. concentrationThe organic layer was concentrated

出典と根拠

ORDレコード
ord-963be81badc04bdb996481458fe0ca4a
出典データセット
uspto-grants-2013_05
特許番号
US08440707B2

反応ノート

読み込み中…