Methanol → Methyl 3-oxocyclobutane-1-carboxylate

HRID 2040620Notes

Reaction equation

HRID 2040620 reaction equation
[CH2:1]1CCC(N=C=NC2CCCCC2)CC1.[O:16]=[C:17]1[CH2:20][CH:19]([C:21]([OH:23])=[O:22])[CH2:18]1.CO>C(Cl)Cl.CN(C1C=CN=CC=1)C>[O:16]=[C:17]1[CH2:20][CH:19]([C:21]([O:23][CH3:1])=[O:22])[CH2:18]1

Participants

6

Reactant 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 13992367Methyl 3-oxocyclobutane-1-carboxylateYield 118.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DCC (5.96 g, 28.95 mmol) in DCM (20 ml) was added dropwise a mixture of 3-oxocyclobutanecarboxylic acid (3.0 g, 26.31 mmol), MeOH (1.68 g, 52.62 mmol) and DMAP (2.57 g, 21.05 mmol) in DCM (30 ml). The reaction mixture was stirred at RT overnight. The mixture was filtrated. The filtrate was washed with 0.5 M HCl solution (50 ml). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by SGC (PE: EA=5:1) to obtain the title compound (4.0 g). 1H N.R (500 MHz, CDCl3): δ 3.77 (s, 3H), 3.42-3.26 (m, 5H) ppm.

Workup

  1. filtrationThe mixture was filtrated
  2. washThe filtrate was washed with 0.5 M HCl solution (50 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by SGC (PE: EA=5:1)

Sources & evidence

ORD record
ord-f5d2b425079740f89966dddbda717cc4
Source dataset
uspto-grants-2013_11
Patent number
US08580762B2

Reaction notes

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