Diethyl Ether → 1,3-Dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptane

HRID 21824Notes

Reaction equation

HRID 21824 reaction equation
[OH-].[Na+].[Cl:3][C:4]1(Cl)[CH2:9][CH2:8][CH2:7][C:6]([Cl:11])([F:10])[CH:5]1O.CC[O:16]CC>O>[Cl:3][C:4]12[O:16][CH:9]1[CH2:8][CH2:7][C:6]([Cl:11])([F:10])[CH2:5]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 189709602,2,6-Trichloro-6-fluorocyclohexanol

Product 1

HCID 189709661,3-Dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.85 g (21.3 mmol) of sodium hydroxide pellets were added in three portions to 1.6 g (7.22 mmol) of pure alcohol 1f in suspension in 22 cm3 of distilled water at 15°-20° C. The reaction mixture was kept at room temperature for 1 h 15 min, 10 cm3 of ether were then added, stirring was continued for 5 min and then the aqueous phase was separated off and extracted with ether (5×25 cm3). The ether phases were combined, dried over magnesium sulfate and filtered, and the solvent was evaporated off. 1.28 g of a liquid, the epoxide 2e, were obtained; the crude yield was 96% (macrobore GC purity>98%).

Workup

  1. waitwas continued for 5 min
  2. customthe aqueous phase was separated off
  3. extractionextracted with ether (5×25 cm3)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-5012092a33f94258a496fa5a096d1aad
Source dataset
uspto-grants-1995_06
Patent number
US05424460

Reaction notes

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