Methanol → HCID 23023468, compound

HRID 2222450Notes

Reaction equation

HRID 2222450 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][C:7]1([C:12]([O:14]C)=[O:13])[CH2:11][CH2:10][CH2:9][O:8]1.B(Br)(Br)Br.CO.O>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH2:6][C:7]1([C:12]([OH:14])=[O:13])[CH2:11][CH2:10][CH2:9][O:8]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 23023492HCID 23023492, compound

Product 1

HCID 23023468HCID 23023468, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 2.50 g of methyl 2-(3-methoxybenzyl)-tetrahydro-2-furancarboxylate in 50 ml of dichloromethane was added 22 ml of a 1 M solution of boron tribromide in dichloromethane at −70° C. under an atmosphere of nitrogen gas. After warming to 0° C., the mixture was cooled again to −70° C., and 20 ml of methanol was added. 200 ml of dichloromethane and 100 ml of water were further added. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated, to give 2.20 g of the title compound.

Workup

  1. temperaturethe mixture was cooled again to −70° C.
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-eaf3494a31374f74b989c26d54d0a7a9
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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