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

HRID 345370Notes

Reaction equation

HRID 345370 reaction equation
O[CH2:2][C:3]([CH2:13][OH:14])([CH2:10][CH2:11][CH3:12])[CH:4]([OH:9])[C:5]([F:8])([F:7])[F:6].C(=O)(OCC)OCC.[OH-].[K+]>C(O)C>[OH:9][CH:4]([C:3]1([CH2:10][CH2:11][CH3:12])[CH2:2][O:14][CH2:13]1)[C:5]([F:6])([F:7])[F:8]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 14797Potassium HydroxideHCID 150219533,3-Di-(hydroxymethyl)-1,1,1-trifluorohexan-2-ol

Product 1

HCID 150219493-(1-Hydroxy-2,2,2-trifluoroethyl)-3-n-propyloxetaneYield 66.2%

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-72bc6af37e2d4962b257c8a5dd7ed60a
Source dataset
uspto-grants-1991_10
Patent number
US05057508

Reaction notes

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