Benzyl Alcohol → Benzyl 3-methylidenecyclobutane-1-carboxylate

HRID 1786282Notes

Reaction equation

HRID 1786282 reaction equation
C(N1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=O.[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)(=O)C.C(OCC)C>[CH2:13]([O:20][C:13]([CH:14]1[CH2:19][C:11](=[CH2:12])[CH2:15]1)=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 57478428Benzyl 3-methylidenecyclobutane-1-carboxylateYield 115.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of 1,1′-carbonyldiimidazole (1.59 g, 9.81 mmol) in ethyl acetate (5 ml) was added in portions to a solution of the product of Preparation 12 (1 g, 8.9 mmol) in ethyl acetate (5 ml). Gentle effervescence was observed. The mixture was stirred at room temperature for about 1.5 hours, benzyl alcohol (1.11 ml, 10.7 mmol) added and stirring continued overnight. The solution was diluted with diethyl ether (20 ml), washed with water (2×10 ml), dried over magnesium sulphate and evaporated in vacuo to a colourless liquid which was purified by filtering through 10 g SiO2, eluting with dichloromethane, to give the title compound as a colourless oil (1.246 g, 69%).

Workup

  1. stirringstirring continued overnight
  2. washwashed with water (2×10 ml)
  3. dry with materialdried over magnesium sulphate
  4. customevaporated in vacuo to a colourless liquid which
  5. customwas purified
  6. filtrationby filtering through 10 g SiO2
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-e1b73198fb504a57abdf39bd7fa3a0f2
Source dataset
uspto-grants-2009_03
Patent number
US07507742B2

Reaction notes

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