Diethyl Carbonate → 3-(1-Hydroxy-2,2,2-trifluoroethyl)-3-n-propyloxetane

HRID 466520Notes

Reaction equation

HRID 466520 reaction equation
[F:1][C:2]([F:10])([F:9])[CH:3]([OH:8])[CH2:4][CH2:5][CH2:6][CH3:7].[C:11](=O)(OCC)[O:12][CH2:13]C.[OH-].[K+]>C(O)C>[OH:8][CH:3]([C:4]1([CH2:5][CH2:6][CH3:7])[CH2:13][O:12][CH2:11]1)[C:2]([F:10])([F:9])[F:1]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 14797Potassium HydroxideHCID 110191001,1,1-Trifluorohexan-2-ol

Product 1

HCID 150219493-(1-Hydroxy-2,2,2-trifluoroethyl)-3-n-propyloxetane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,3-di-hydroxymethyl)-1,1,1-trifluorohexan-2-ol (2.8 g.), diethyl carbonate (1.6 ml.), potassium hydroxide (0.1 g) and dry ethanol (4.0 mls) was refluxed gently (oil bath 110°), under a current of nitrogen, for 30 minutes. The ethanol was then removed by distillation. Distillation gave (3-(1-hydroxy-2,2,2-trifluoroethyl)-3-n-propyloxetane (1.7 g.), a colourless oil (b.p. 112°, 20-25 m.m.).

Workup

  1. temperaturewas refluxed gently (oil bath 110°)
  2. customThe ethanol was then removed by distillation
  3. distillationDistillation

Sources & evidence

ORD record
ord-7bce8108e5124a42a646f99fd4e05b9e
Source dataset
uspto-grants-1992_10
Patent number
US05157029

Reaction notes

Loading…