1,3-Difluoroacetone → HCID 86706177, compound

HRID 2176328Notes

Reaction equation

HRID 2176328 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]([CH2:10][OH:11])([CH2:8][OH:9])[CH:6]=[CH2:7])[CH3:2].[F:13][CH2:14][C:15]([CH2:17][F:18])=O>>[CH2:1]([O:3][C:4]([C:5]1([CH:6]=[CH2:7])[CH2:8][O:9][C:15]([CH2:17][F:18])([CH2:14][F:13])[O:11][CH2:10]1)=[O:12])[CH3:2]

Participants

3

Reactant 2

HCID 2283971,3-DifluoroacetoneHCID 86706156HCID 86706156, compound

Product 1

HCID 86706177HCID 86706177, compoundYield 77.5%

Conditions

Temperature
100 °C

Procedure

A vial was loaded with 2,2-bis-hydroxymethyl-but-3-enoic acid ethyl ester (0.88 g, 5.05 mmol), 1,3-difluoroacetone (0.95 g, 10.1 mmol) and para-toluene-4-sulfonic acid monohydrate (0.96 g, 5.05 mmol). The vial was sealed and heated in a microwave reactor at 100° C. for 15 min. The resultant brown oil was partitioned between dichloromethane and aqueous sodium bicarbonate solution. The organic layer was filtered through a hydrophobic frit and evaporated to give a brown oil (0.98 g). The oil was purified by silica gel chromatography using iso-hexanes/ethyl acetate 3:1 to yield the title compound (0.619 g, 74%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ 1.31 (t, J=7.1 Hz, 3H), 3.96 (d, J=12.0 Hz, 2H), 4.27 (q, J=7.1 Hz, 2H), 4.34-4.69 (m, 6H), 5.22-5.35 (m, 2H), 5.67-5.79 (m, 1H).

Workup

  1. customThe vial was sealed
  2. customThe resultant brown oil was partitioned between dichloromethane and aqueous sodium bicarbonate solution
  3. filtrationThe organic layer was filtered through a hydrophobic frit
  4. customevaporated

Sources & evidence

ORD record
ord-b1ac152e9b3345f88746f69ca1d69176
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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