Methanol → Methyl 3-oxocyclobutane-1-carboxylate

HRID 1692912Notes

Reaction equation

HRID 1692912 reaction equation
[CH:1]1(N=C=NC2CCCCC2)CCCCC1.C(Cl)Cl.[O:19]=[C:20]1[CH2:23][CH:22]([C:24]([OH:26])=[O:25])[CH2:21]1.CO>CN(C)C1C=CN=CC=1>[O:19]=[C:20]1[CH2:23][CH:22]([C:24]([O:26][CH3:1])=[O:25])[CH2:21]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344Dichloromethane2×HCID 10868DicyclohexylcarbodiimideHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 13992367Methyl 3-oxocyclobutane-1-carboxylateYield 80.64%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of N,N′-dicyclohexylcarbodiimide (7.17 g, 0.0347 mol) in methylene chloride (8 mL, 0.1 mol) was added dropwise to a stirred mixture of 3-oxocyclobutanecarboxylic acid (3.6 g, 0.032 mol), methanol (2.6 mL, 0.063 mol) and 4-dimethylaminopyridine (3.08 g, 0.0252 mol) in methylene chloride (20 mL, 0.2 mol). The mixture was stirred at rt for 24 h, then filtered through Celite. The filtrate was washed with 0.5 M HCl and sat. sodium bicarbonate, dried and concentrated to dry. The residue was purified on silica gel, eluting with 0 to 40% EtOAc in hexane, to give the desired ester (3.26 g, 80.64%). 1H NMR (CDCl3, 400 MHz): 3.78 (s, 3H), 3.43˜3.20 (5H, m) ppm.

Workup

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with 0.5 M HCl and sat. sodium bicarbonate
  3. customdried
  4. concentrationconcentrated
  5. customto dry
  6. customThe residue was purified on silica gel
  7. washeluting with 0 to 40% EtOAc in hexane

Sources & evidence

ORD record
ord-ab65ff2e9a6a4c23b37b90579c932fe3
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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