Acetone → (4'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-yl)methanol

HRID 2280670Notes

Reaction equation

HRID 2280670 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH:23]=[O:24])[CH:17]=2)=[C:11]([CH3:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CC(C)=O>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH3:25])[C:12]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH2:23][OH:24])[CH:17]=2)=[C:13]([CH3:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 897017664'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-carbaldehyde

Product 1

HCID 89701768(4'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-yl)methanolYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4′-(Benzyloxy)-4-fluoro-2′,6′-dimethylbiphenyl-3-carbaldehyde 18a (390 mg, 1.17 mmol) were dissolved in 5 mL of methanol, followed by addition of sodium borohydride (66 mg, 1.75 mmol). The reaction solution was stirred for 30 minutes. The resulting solution was mixed with 10 mL of acetone and concentrated under reduced pressure. The residue was mixed with 10 mL of water and extracted with ethyl acetate (10 mL×3). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure to obtain the crude title compound (4′-(benzyloxy)-4-fluoro-2′,6′-dimethylbiphenyl-3-yl)methanol 18b (370 mg) as a colorless slime, which was directly used in the next step without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was mixed with 10 mL of water
  3. extractionextracted with ethyl acetate (10 mL×3)
  4. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  5. dry with materialdried with anhydrous magnesium sulphate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-acaeccbf54c1473bbc74de5340aae9ca
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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