Benzyl Alcohol → HCID 11984508, compound

HRID 926218Notes

Reaction equation

HRID 926218 reaction equation
[F:1][CH:2]([F:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(O)[C:10]1[CH:15]=[CH:14]C=[CH:12][CH:11]=1.B(F)(F)F.CCOCC>>[F:1][CH:2]([F:8])[C:3]([O:5][CH2:6][C:7]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1)=[O:4]

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 8000Boron trifluoride etherateHCID 9961Ethyl difluoroacetate

Product 1

HCID 11984508HCID 11984508, compound

Conditions

Temperature
75 °C

Procedure

To a dried round bottom flask was added ethyl 2,2-difluoroacetate (25 g, 0.20 mol), benzyl alcohol (62.6 mL, 0.60 mol) and boron trifluoride etherate (2.5 mL, 0.02 mmol) under nitrogen atmosphere. The reaction mixture was stirred at 75° C. overnight. The mixture was quenched with saturated aqueous NaHCO3, and then diluted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give benzyl 2,2-difluoroacetate. 1H-NMR: 400 MHz, (CDCl3) δ 7.39-7.29 (m, 4H), 5.93 (t, J=52.8 Hz, 1H), 5.31 (s, 2H).

Workup

  1. customThe mixture was quenched with saturated aqueous NaHCO3
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-629f275c5c374a83926d9ca8757e08a3
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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