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

HRID 237265노트

반응식

HRID 237265 반응식
[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

참가 물질

5

반응물 2

HCID 15194646-Fluoro-1-indanoneHCID 4311764Sodium borohydride

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 887Methanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-644ed4a1df314c70b61439dc48c28ab4
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642583B2

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