Formaldehyde → Ethyl 2,2-difluoro-3-hydroxypropanoate

HRID 36584

Reaction equation

HRID 36584 reaction equation
[CH2:1]=[O:2].[F:3][C:4]([F:11])(Br)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl-].[NH4+]>O1CCCC1.[Zn]>[F:3][C:4]([F:11])([CH2:1][OH:2])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 2758828Ethyl 2,2-difluoro-3-hydroxypropanoate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of paraformaldehyde (4.5 g, 50 mmol), ethyl difluorobromoacetate (10.2 g, 50 mmol) and activated zinc dust (3.3 g, 40 mmol) in anhydrous tetrahydrofuran was heated under reflux for 0.5 h. Then the mixture was treated with a saturated aqueous solution of ammonium chloride and extracted with diethyl ether. After usual work-up the desired compound ethyl 2,2-difluoro-3-hydroxypropionate was obtained by flash chromatography on silica gel (ethyl acetate:hexane; 25:75) (4.1 g, 53%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 0.5 h
  3. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-07cd20d9a5744d628778aeaa05aa92ac
Source dataset
uspto-grants-1995_05
Patent number
US05416076

Linked notes

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