Water → HCID 14720911, compound

HRID 2073476Notes

Reaction equation

HRID 2073476 reaction equation
[Cl:1][CH:2]1[CH2:5][CH:4]([CH2:6][OH:7])[CH2:3]1.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[H-].[Na+].O>CN(C)C=O>[Cl:1][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

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 13813819(3-Chlorocyclobutyl)methanol

Product 1

HCID 14720911HCID 14720911, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-chlorocyclobutanemethanol (17.3 g, 0.143 mole) and benzylbromide (26.96 g, 0.158 mole) in dry dimethylformamide (123 ml) was stirred at room temperature under an argon atmosphere and a 60% suspension of sodium hydride (6.31 g 0.158 g mole) was added. The reaction was stirred at ambient temperature for 22.5 hours. The reaction mixture was poured into 600 ml of water and the aqueous mixture extracted with ethyl acetate (4×500 ml). The ethyl acetate extracts were combined and dried over anhydrous sodium sulfate and the ethyl acetate evaporated in vacuo yielding the crude product as a yellow oil. The material was purified on a 2-liter Merck silica gel column eluting with 3 liters of hexane, followed by 5% ethyl acetate/hexane. The fractions containing the desired product were combined and the volatiles evaporated in vacuo yielding 28.6 g of the title compound as a pale yellow oil.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 22.5 hours
  2. extractionthe aqueous mixture extracted with ethyl acetate (4×500 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe ethyl acetate evaporated in vacuo
  5. customyielding the crude product as a yellow oil
  6. customThe material was purified on a 2-liter Merck silica gel column
  7. washeluting with 3 liters of hexane
  8. additionThe fractions containing the desired product
  9. customthe volatiles evaporated in vacuo

Sources & evidence

ORD record
ord-f3238f73d2f04f0baa996c6989b60f6c
Source dataset
uspto-grants-1990_04
Patent number
US04918075

Reaction notes

Loading…