Methanol → HCID 18340683, compound

HRID 1369231Notes

Reaction equation

HRID 1369231 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=3[O:8][C:7]=2[CH:23]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:12][CH:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]3[CH:19]=[CH:20][CH:21]=[CH:22][C:9]=3[O:8][C:7]=2[CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 18340684HCID 18340684, compound

Product 1

HCID 18340683HCID 18340683, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl (±)-10,11-dihydro-3-methoxydibenzo[b,f]oxepine-10-acetate (523 mg, 1.68 mmole) in CH2Cl2 (6.8 mL) was added dropwise to a cold solution of BBr3 in CH2Cl2 (1.0 M, 6.7 mL, 6.7 mmole) at 0° C. under argon. The reaction was stirred for 20 min, then CH3OH (7 mL) was added carefully. The mixture was concentrated and the residue was flash chromatographed on silica gel (15-20% EtOAc/hexanes) to afford the title compound (407 mg, 89%) as a pale yellow oil: MS (ES) m/e 299 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed on silica gel (15-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7f36369d40de41f584a816d3ae3ff484
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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