Sodium Hydroxide → 2-Allyl-1,3,3-trichloro-7-oxabicyclo[4.1.0]heptane

HRID 21832Notes

Reaction equation

HRID 21832 reaction equation
ClC12[O:8]C1CCC(Cl)(F)C2.[CH2:11]([C:14]1(O)[C:19]([Cl:21])([Cl:20])[CH2:18][CH2:17][CH2:16][C:15]1([Cl:23])Cl)[CH:12]=[CH2:13].[OH-].[Na+]>O>[CH2:11]([CH:14]1[C:19]([Cl:21])([Cl:20])[CH2:18][CH2:17][CH:16]2[C:15]1([Cl:23])[O:8]2)[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 189709581-Allyl-2,2,6,6-tetrachlorocyclohexanolHCID 189709661,3-Dichloro-3-fluoro-7-oxabicyclo[4.1.0]heptane

Product 1

HCID 189709622-Allyl-1,3,3-trichloro-7-oxabicyclo[4.1.0]heptaneYield 92%

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 1.12 g (4.03 mmol) of crude alcohol 1l, 5.5 cm3 of distilled water and 0.6 g (12.5 mmol) of sodium hydroxide; reaction time was 1 h 15 min followed by ether extraction; the crude product was employed as such (crude yld=90.5%) or purified by flash chromatography on silica (eluent: ether/petroleum ether=3/97): 0.89 g of epoxide 2j were obtained, that was a 92% yield (macrobore GC purity>98.6%).

Workup

  1. customreaction time
  2. extractionfollowed by ether extraction
  3. custompurified by flash chromatography on silica (eluent: ether/petroleum ether=3/97)

Sources & evidence

ORD record
ord-90beb8ed5a824ea291a9660494e4b04a
Source dataset
uspto-grants-1995_06
Patent number
US05424460

Reaction notes

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