Boron trifluoride etherate → HCID 67931226, compound

HRID 982114Notes

Reaction equation

HRID 982114 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:21])[CH2:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:24](OC)[CH2:25][Br:26].B(F)(F)F.CCOCC.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:11][C:12]2[C:13]([O:19][CH3:20])=[CH:14][CH:15]=[C:16]([CH3:18])[C:17]=2[C@H:24]([CH2:25][Br:26])[O:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 20069105HCID 20069105, compound

Product 1

HCID 67931226HCID 67931226, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-benzyloxy-3-(2'-methoxy-5'-methylphenyl)-2-propanol (3.4 g, 12 mmol), from Step 1, and bromoacetaldehyde dimethyl acetal (1.7 mL, 14 mmol) in 25 mL of methylene chloride is cooled to 0° C. Boron trifluoride etherate (3.6 mL, 29 mmol) is added dropwise and the reaction mixture is stirred for 1.5 h. The resultant dark brown solution is poured into 50 mL of 10% aqueous sodium carbonate solution and the aqueous solution is extracted with 3×50 mL of diethyl ether. The combined ether extracts are washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give the title compound.

Workup

  1. extractionthe aqueous solution is extracted with 3×50 mL of diethyl ether
  2. washThe combined ether extracts are washed with saturated aqueous sodium bicarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4f4ff149c4664f58866595424cf1c16f
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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