Boron trifluoride etherate → HCID 15428708, compound

HRID 1585054Notes

Reaction equation

HRID 1585054 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=1)[O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].[C:18]1([CH:24](OC(=N)C(Cl)(Cl)Cl)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.B(F)(F)F.CCOCC>C(Cl)(Cl)Cl.C1CCCCC1>[C:18]1([CH:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[O:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]2[CH:7]=[C:8]([CH:15]=[CH:16][CH:17]=2)[O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 15428707HCID 15428707, compoundHCID 21221403HCID 21221403, compound

Product 1

HCID 15428708HCID 15428708, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-(4-hydroxybutyl)phenoxyacetate (372 mg) and diphenylmethyltrichloroacetoimidate (771 mg) in chloroform (4 ml) and cyclohexane (8 ml) was added a catalytic amount of boron trifluoride etherate at 0° C. After being stirred for 30 min at 0° C., the mixture was quenched by addition of a saturated aqueous solution of sodium bicarbonate, and extracted with ether. The extract was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (343 mg) having the following physical data.

Workup

  1. customthe mixture was quenched by addition of a saturated aqueous solution of sodium bicarbonate
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-f3e17701e39642a09beae27c4f68304e
Source dataset
uspto-grants-1999_08
Patent number
US05935985

Reaction notes

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