Water → HCID 11008421, compound

HRID 2073477Notes

Reaction equation

HRID 2073477 reaction equation
Cl[CH:2]1[CH2:5][CH:4]([CH2:6][O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.CC(C)([O-])C.[K+].O>CS(C)=O>[CH:4]1([CH2:6][O:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][CH:2]=[CH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 14720911HCID 14720911, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11008421HCID 11008421, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

[[(3-Chlorocyclobutyl)methoxy]methyl]benzene 82 g, 0.39 mole) in 390 ml of dry dimethylsulfoxide was slowly added to a solution of potassium t-butoxide (132 g, 1.17 mole) in 390 ml of dry dimethylsulfoxide in a water-bath at 18° C. under a dry argon atmosphere. After stirring for 1 hour at room temperature, the reaction mixture was poured into 1600 ml of water and extracted with ether (3×1000 ml). The combined ether extracts were back-extracted with water (4×2000 ml), the extracts were then dried over sodium sulfate, and the volatiles were removed in vacuo. The crude product was divided into two equal portions and each portion was purified on separate 3.5 liter Merck silica columns, eluting with 3% ethyl acetate-hexane. Appropriate fractions were combined and the solvents removed in vacuo yielding 60.0 g of the title compound as a colorless liquid.

Workup

  1. extractionextracted with ether (3×1000 ml)
  2. extractionThe combined ether extracts were back-extracted with water (4×2000 ml)
  3. dry with materialthe extracts were then dried over sodium sulfate
  4. customthe volatiles were removed in vacuo
  5. customeach portion was purified
  6. customon separate 3.5 liter Merck silica columns
  7. washeluting with 3% ethyl acetate-hexane
  8. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-ec726bc890884cca94b8659e7d7c55a8
Source dataset
uspto-grants-1990_04
Patent number
US04918075

Reaction notes

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