Methanol → Methyl 3-oxocyclobutane-1-carboxylate

HRID 1966143Notes

Reaction equation

HRID 1966143 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-c2d79128c70a405b9b58200327575b05
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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