Boron tribromide → Methyl (5-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate

HRID 1821055노트

반응식

HRID 1821055 반응식
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:10]2>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:10]2

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 71710973Methyl (5-methoxy-2,3-dihydro-1H-inden-1-yl)acetate

생성물 1

HCID 53438903Methyl (5-hydroxy-2,3-dihydro-1H-inden-1-yl)acetate수율 92.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A 1.0 M solution of boron tribromide in dichloromethane (22.7 mL, 22.7 mmol) was added to an ice-cold solution of methyl (R/S)-(5-methoxy-indan-1-yl)acetate (2.00 g, 9.08 mmol, from Step B) in dichloromethane (15 mL). The cooling bath was removed and the reaction mixture stirred at ambient temperature. After 1 hr, the reaction mixture was slowly transferred to an ice-cold solution of methanol (50 mL). Methanol was removed in vacuo, and the residue was partitioned between EtOAc and sat. NaH2PO4. The organic layer was washed with H2O, brine, and dried over MgSO4. The mixture was filtered, concentrated in vacuo and purified by flash chromatography (15, 20% EtOAc/hexanes) on SiO2 to afford 1.74 g of the title compound: 1H NMR (CDCl3) δ 1.72-1.79 (m, 1H), 2.35-2.42 (m, 1H), 2.46 (dd, 1H, J=8.5, 15.3 Hz), 2.76 (dd, 1H, J=5.9, 15.3 Hz), 2.80-2.92 (m, 2H), 3.50-3.55 (m, 1H), 3.75 (s, 3H), 5.63-5.86 (brs, 1H), 6.67 (dd, 1H, J=2.4, 8.1 Hz), 6.74 (d, 1H, J=2.0 Hz), 7.01 (d, 1H, J=8.3 Hz).

후처리

  1. customThe cooling bath was removed
  2. customMethanol was removed in vacuo
  3. customthe residue was partitioned between EtOAc and sat. NaH2PO4
  4. washThe organic layer was washed with H2O, brine
  5. dry with materialdried over MgSO4
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography (15, 20% EtOAc/hexanes) on SiO2

출처 및 근거

ORD 기록
ord-db5dc891434b488083bd335aeadd3e7f
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605171B2

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