Ethanol → HCID 21110628, compound

HRID 1766689Notes

Reaction equation

HRID 1766689 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[O:30]C)[O:7][C:8]1[C:9]([CH3:26])=[CH:10][C:11]([NH:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]2[C:16]=1[CH2:15][CH2:14][CH2:13]2)(=[O:3])[CH3:2].B(Cl)(Cl)Cl.C(O)C>ClCCl>[C:1]([C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[OH:30])[O:7][C:8]1[C:9]([CH3:26])=[CH:10][C:11]([NH:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]2[C:16]=1[CH2:15][CH2:14][CH2:13]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 25135Boron TrichlorideHCID 21110629HCID 21110629, compound

Product 1

HCID 21110628HCID 21110628, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl N-[7-(3-acetyl-4-methoxyphenoxy)-6-methylindan-4-yl]malonamate (268 mg) in dichloromethane (15 mL) was added a 1 mol/L solution of boron trichloride in dichloromethane (1.9 mL) under ice-cooling, and the mixture was stirred at room temperature for 3 days. Ethanol was added to the reaction mixture, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1−1/1) to give the title compound (183 mg).

Workup

  1. temperaturecooling
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1−1/1)

Sources & evidence

ORD record
ord-c9612923b6a04d4ab2d21031cedee0d0
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

Loading…