Sodium Hydroxide → 1,3,3-Trichloro-2-vinyl-7-oxabicyclo[4.1.0]heptane

HRID 21831Notes

Reaction equation

HRID 21831 reaction equation
ClC12[O:8]C1CCC(Cl)(F)C2.[CH:11]([C:13]1(O)[C:18]([Cl:20])([Cl:19])[CH2:17][CH2:16][CH2:15][C:14]1([Cl:22])Cl)=[CH2:12].[OH-].[Na+]>O>[Cl:22][C:14]12[O:8][CH:15]1[CH2:16][CH2:17][C:18]([Cl:20])([Cl:19])[CH:13]2[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 189709661,3-Dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptaneHCID 199335341-Vinyl-2,2,6,6-tetrachlorocyclohexanol

Product 1

HCID 189709491,3,3-Trichloro-2-vinyl-7-oxabicyclo[4.1.0]heptaneYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The same procedure was employed as for the preparation of 2e in Example 17: it was performed with 1.14 g (4.32 mmol) of pure alcohol 1k, 12 cm3 of distilled water and 0.5 g (12.5 mmol) of sodium hydroxide; reaction time was 1 h 15 min; ether extraction (4×25 cm3); the crude product was employed as such (crude yld=90.5%) or purified by flash chromatography on silica (eluent: ether/petroleum ether=3/97): 0.88 g of epoxide 2i were obtained, that was a 90% yield (macrobore GC purity>98.6%)

Workup

  1. customreaction time
  2. extractionether extraction (4×25 cm3)
  3. custompurified by flash chromatography on silica (eluent: ether/petroleum ether=3/97)

Sources & evidence

ORD record
ord-33ca5fd2d96a4b36a3e4e6ed81bdbc85
Source dataset
uspto-grants-1995_06
Patent number
US05424460

Reaction notes

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