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

HRID 1821055Notes

Reaction equation

HRID 1821055 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-db5dc891434b488083bd335aeadd3e7f
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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