Methanol → 3-(3-Chloro-benzo[b]thiophen-2-yl)-propan-1-ol

HRID 1749227ノート

反応式

HRID 1749227 の反応式
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[C:7]=1[Cl:15].[Li+].[BH4-].CO.[OH-].[Na+]>CCOCC>[Cl:15][C:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[S:10][C:6]=1[CH2:5][CH2:4][CH2:3][OH:2]

参加物

6

反応物 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 667607513-(3-Chloro-benzo[b]thiophen-2-yl)-propionic acid methyl ester

生成物 1

HCID 219644313-(3-Chloro-benzo[b]thiophen-2-yl)-propan-1-ol収率 79%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

An ice cold solution of 3.63 g (14.3 mmol) of 15 in 60 mL of ether was treated with LiBH4 (621 mg, 28.5 mmol) and methanol (2 mL). After 30 min., 30 mL of 0.5 M NaOH solution was added. The mixture was extracted with ethyl acetate (2×25 mL) and the combined ethyl acetate solution washed with brine (50 mL), dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel (5-20% ethyl acetate/hexane) to give 2.57 g (11.3 mmol, 79%) of the alcohol (16).

後処理

  1. extractionThe mixture was extracted with ethyl acetate (2×25 mL)
  2. washthe combined ethyl acetate solution washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (5-20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-e2a22df8bc0f423392a971e7087ce02e
出典データセット
uspto-grants-2015_10
特許番号
US09156810B2

反応ノート

読み込み中…