Acetone → HCID 68460054, compound

HRID 501795Notes

Reaction equation

HRID 501795 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH2:6][C:7]1([C:12](O)=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]1.CC(C)=O.O.C(OCC)(=O)C>O1CCCC1.B>[OH:13][CH2:12][C:7]1([CH2:6][C:5]2[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 962Water2×HCID 8857Ethyl AcetateHCID 68458347HCID 68458347, compound

Product 1

HCID 68460054HCID 68460054, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 6331BoraneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.50 g of 1-[3-methoxy-4-(methoxycarbonyl)-benzyl]cyclopentanecarboxylic acid was dissolved in 15 mL of tetrahydrofuran, to which 10.3 mL of a 1M solution of borane in tetrahydrofuran was added dropwise at 5 to 10° C., and then this mixture was stirred for one hour at room temperature. Then, acetone and water were successively added dropwise to the reaction mixture, which was added to a mixture of ethyl acetate and water, and the organic phase was separated therefrom. After the resultant organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate, water, and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:1] to yield 0.564 g of methyl 4-{[1-(hydroxymethyl) cyclopentyl]methyl}-2-methoxybenzoate as colorless oil.

Workup

  1. additionwas added dropwise at 5 to 10° C.
  2. customthe organic phase was separated
  3. washAfter the resultant organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate, water
  4. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled out under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:1]

Sources & evidence

ORD record
ord-80d3efba2ce947e5a70b481ae6ec1173
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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