Water → HCID 58047073, compound

HRID 1888747Notes

Reaction equation

HRID 1888747 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[C:8]([F:15])[CH:7]=2)[CH2:3][CH2:2]1.B.C1COCC1.O>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([CH2:10][OH:11])=[C:8]([F:15])[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 962Water2×HCID 2723981Borane;tetrahydrofuranHCID 23090959HCID 23090959, compound

Product 1

HCID 58047073HCID 58047073, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(cyclopropylmethoxy)-2-fluorobenzoic acid (5.00 g, 23.8 mmol) in THF (100 mL) was added dropwise 1 M borane-THF solution (54.7 mL, 54.7 mmol), and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was slowly added dropwise water (100 mL). To this solution was further added water, and the mixture was extracted with ethyl acetate. The extract was washed with 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solution was purified by basic silica gel column chromatography (ethyl acetate), and the obtained residue was triturated with hexane to give the title compound (4.08 g, yield 87%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 10% aqueous potassium carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solution was purified by basic silica gel column chromatography (ethyl acetate)
  5. customthe obtained residue was triturated with hexane

Sources & evidence

ORD record
ord-75e688c87b004d30831f51b3ca7bb20c
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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