Borane → Ethyl 2,2-difluoro-4-hydroxybutanoate

HRID 905010Notes

Reaction equation

HRID 905010 reaction equation
B.[F:2][C:3]([F:13])([CH2:9][C:10](O)=[O:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5]>O1CCCC1>[F:2][C:3]([F:13])([CH2:9][CH2:10][OH:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 6331BoraneHCID 13189244HCID 13189244, compound

Product 1

HCID 13189245Ethyl 2,2-difluoro-4-hydroxybutanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 123.0 mL (0.123 mol) of 1.0 M of borane in tetrahydrofuran was added dropwise at 0° to a mixture of 12.4 g (0.068 mol) of ethyl 2,2-difluoro-3-carboxypropionate in 70 mL of dry tetrahydrofuran. The reaction mixture was stirred at 0° for 18 hr then was quenched by adding 40 mL of water dropwise. The solution was saturated with solid sodium chloride and the product was isolated with ether. The ether layers were washed with saturated aqueous sodium bicarbonate and brine. The solution was dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness to yield ethyl 2,2-difluoro-4-hydroxybutyrate. NMR (CDCl3) δ4.32 (quartet, 2, 2, J=7 Hz), 3.87 (triplet, 2, J=6 Hz), 2.36 (multiplet, 2) and 1.35 ppm (triplet, 3, J=7 Hz).

Workup

  1. customthen was quenched
  2. additionby adding 40 mL of water dropwise
  3. customthe product was isolated with ether
  4. washThe ether layers were washed with saturated aqueous sodium bicarbonate and brine
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-51d2810bac4c41ddad1d6f39e3301d03
Source dataset
uspto-grants-1983_12
Patent number
US04421690

Reaction notes

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