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

HRID 1749227노트

반응식

HRID 1749227 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-e2a22df8bc0f423392a971e7087ce02e
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156810B2

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