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

HRID 399335Notes

Reaction equation

HRID 399335 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%) MW: 227.519; 1H NMR: 6.75-6.30 (m, 1H); 5.80-5.45 (m, 2H); 3.00-1.25 (m, 6H). 13C NMR: 126.1 (C7); 123.1 (C8); 88.35 (C3); 85.5 (C1); 70.0 (C2); 39.75 (C4); 32.4 (C6); 18.3 (C5). IR in cm-1 (film): 1080-940-875-785-735.

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-ca9025e201a449efa02f9434dbf235b9
Source dataset
uspto-grants-1998_10
Patent number
US05817890

Reaction notes

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