Ethyl Acetate → (5-Fluoro-1-benzothiophen-2-yl)methanol

HRID 1843958

반응식

HRID 1843958 반응식
CC(C[AlH]CC(C)C)C.[F:10][C:11]1[CH:23]=[CH:22][C:14]2[S:15][C:16]([C:18](OC)=[O:19])=[CH:17][C:13]=2[CH:12]=1.C(OCC)(=O)C>C1COCC1.CCCCCC>[F:10][C:11]1[CH:23]=[CH:22][C:14]2[S:15][C:16]([CH2:18][OH:19])=[CH:17][C:13]=2[CH:12]=1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 22473847Methyl 5-fluoro-1-benzothiophene-2-carboxylate

생성물 1

HCID 36995594(5-Fluoro-1-benzothiophen-2-yl)methanol수율 83.33%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-10 °C

실험 절차

DIBAL-H (59.4 mL, 59.41 mmol) was added to a solution of methyl 5-fluorobenzo[b]thiophene-2-carboxylate (I-50a: 2.5 g, 11.882 mmol) in THF (75 mL) at −70° C. and the resulting reaction mass was stirred at −10° C. for 2 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was quenched with methanol at −70° C. and concentrated under reduced pressure. The crude residue obtained was partitioned between water and ethyl acetate. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (15% ethyl acetate in hexane) afforded 1.8 g of the product (83.33% yield).

후처리

  1. customthe resulting reaction mass
  2. customThe reaction mass was quenched with methanol at −70° C.
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue obtained
  5. customwas partitioned between water and ethyl acetate
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto afford the crude product
  9. customPurification by column chromatography on silica gel (15% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-5f9944555000483286c8ad2335b14e60
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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