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

HRID 1843958ノート

反応式

HRID 1843958 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-10 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5f9944555000483286c8ad2335b14e60
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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