1-Indanone, 4-bromo- → 4-Bromo-1-indanol

HRID 1053749노트

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HRID 1053749 반응식
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[BH4-].[Na+]>CCO>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[OH:11]

참가 물질

4

반응물 2

HCID 987131-Indanone, 4-bromo-HCID 4311764Sodium borohydride

생성물 1

HCID 133302084-Bromo-1-indanol

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

To a stirring solution of 4-bromoindanone (3 g, 14.2 mmol) in anhydrous EtOH (30 mL) were added sodium borohydride (0.36 g, 9.5 mmol) and silica gel (2 g) at 0° C. The reaction was stirred at 0° C. for 20 min and was allowed to stir at room temperature for 2 h. The reaction mixture was quenched with saturated NaHCO3 and concentrated to remove EtOH. The aqueous layer was extracted with EA and the organic phase was dried over MgSO4. After concentration, the crude product was purified by chromatography (EA/hexane) to yield 4-bromo-2,3-dihydro-1H-inden-1-ol INT-28 (2.56 g, 85%) as white solid. LCMS-ESI (m/z) calculated for C9H9BrO: 213.1; found 195.0 [M−H2O]+, tR=3.07 min. 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J=7.9, 1H), 7.27 (d, J=7.4, 1H), 7.05 (t, J=7.7, 1H), 5.23 (t, J=6.2, 1H), 3.00 (ddd, J=16.6, 8.8, 4.6, 1H), 2.84-2.66 (m, 1H), 2.45 (dddd, J=13.2, 8.4, 7.0, 4.6, 1H), 1.96-1.70 (m, 2H).

후처리

  1. stirringto stir at room temperature for 2 h
  2. customThe reaction mixture was quenched with saturated NaHCO3
  3. concentrationconcentrated
  4. customto remove EtOH
  5. extractionThe aqueous layer was extracted with EA
  6. dry with materialthe organic phase was dried over MgSO4
  7. concentrationAfter concentration
  8. customthe crude product was purified by chromatography (EA/hexane)

출처 및 근거

ORD 기록
ord-fa3a840427614c20903639e518e68dd1
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394264B2

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