Vinyl butyrate → 2-(Trifluoromethyl)-1,2,3-propanetriol

HRID 886706Notes

Reaction equation

HRID 886706 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH2:6][OH:7])[CH2:4][OH:5].[C:11]([O:16]C=C)(=O)[CH2:12][CH2:13][CH3:14]>>[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH2:6][OH:7])[CH2:4][OH:5].[C:11]([O:5][CH2:4][C:3]([CH2:6][O:7][C:11](=[O:16])[CH2:12][CH2:13][CH3:14])([OH:8])[C:2]([F:10])([F:9])[F:1])(=[O:16])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 31247Vinyl butyrateHCID 574449922-(Trifluoromethyl)-1,2,3-propanetriol

Product 2

HCID 574449922-(Trifluoromethyl)-1,2,3-propanetriolHCID 866454052-[(Butanoyloxy)methyl]-3,3,3-trifluoro-2-hydroxypropyl butanoate

Procedure

In parallel reactions, a mixture of 2-(trifluoromethyl)-1,2,3-propanetriol (100 mg), Amano PS onto Sepabeads (100 mg), vinyl butyrate (0.3 ml) and solvent (as shown in table 1 below) (1 ml) was shaken at room temperature. The reactions were analysed by 19F NMR after 42 hours to give 2-(trifluoromethyl)-1,2,3-propanetriol (triol)/title compound/2-[(butanoyloxy)methyl]-3,3,3-trifluoro-2-hydroxypropyl butanoate (diester) peak ratios shown in table 1 below.

Sources & evidence

ORD record
ord-a97802cd86894eeb81b94782d75d1ed0
Source dataset
uspto-grants-2012_08
Patent number
US08247377B2

Reaction notes

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