Benzyl Alcohol → Benzyl 3-oxocyclobutane-1-carboxylate

HRID 715128Notes

Reaction equation

HRID 715128 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=O.[O:13]=[C:14]1[CH:16]([C:17]([OH:19])=[O:18])[CH2:15]1.[CH2:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[O:13]=[C:14]1[CH2:15][CH:16]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:1]1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 682631,1'-CarbonyldiimidazoleHCID 216149313-Oxo-cyclopropane carboxylic acid

Product 1

HCID 15830669Benzyl 3-oxocyclobutane-1-carboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Slowly add carbonyldiimidazole (42.6 g, 263 mmol) to a solution of 3-oxo-cyclopropane carboxylic acid (25.0 g, 219 mmol) in DCM (500 mL), stir at RT for 2 h, add benzyl alcohol (24.17 g, 223 mmol) and stir at RT for 16 h. Add water, extract with DCM (2×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify by silica gel chromatography (EtOAc/Hex) to afford the title compound (29.5 g, 66%) as a colorless syrup. 1H NMR (400 MHz, DMSO-d6): δ 7.38-7.35 (m, 5H); 5.14 (s, 2H); 3.62 (m, 5H); MS (ESI) m/z: 227.1 (M+Na−).

Workup

  1. extractionAdd water, extract with DCM (2×)
  2. washwash the combined organics with brine
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate to dryness
  5. custompurify by silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-f4f6032abf594eb796bfb7ca89c8d925
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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