6-Fluoro-1-indanone → 6-fluoro-2,3-dihydro-1H-inden-1-ol

HRID 237265ノート

反応式

HRID 237265 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>ClCCCl.CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:11])=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 15194646-Fluoro-1-indanoneHCID 4311764Sodium borohydride

生成物 1

HCID 613834996-fluoro-2,3-dihydro-1H-inden-1-ol収率 97.6%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 887Methanol溶媒

実験手順

To a solution of 6-fluoro-indan-1-one (0.50 g, 3.3 mmol) in DCE (10 mL) and MeOH (10 mL) was added NaBH4 (0.25 g, 6.6 mmol). After 30 min the reaction was quenched with H2O (10 mL) and extracted with CH2Cl2 (3×20 mL). The organic layers were combined and dried to give the title compound (0.49 g, 97%). MS (ESI): mass calcd. for C9H7FO, 150.1; m/z found, 151.4 [M+H]+. 1H NMR (CDCl3): 7.23-7.13 (m, 1H), 7.09 (dd, J=8.6, 2.5 Hz, 1H), 6.99-6.90 (m, 1H), 5.21 (t, J=6.3 Hz, 1H), 3.13-2.91 (m, 1H), 2.85-2.68 (m, 1H), 2.63-2.44 (m, 1H), 2.09-1.74 (m, 2H).

後処理

  1. customAfter 30 min the reaction was quenched with H2O (10 mL)
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. customdried

出典と根拠

ORDレコード
ord-644ed4a1df314c70b61439dc48c28ab4
出典データセット
uspto-grants-2014_02
特許番号
US08642583B2

反応ノート

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