Methanol → Methyl 3-oxocyclobutane-1-carboxylate

HRID 511580Notes

Reaction equation

HRID 511580 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-34bc96eefecf4993946c57d12956a804
Source dataset
uspto-grants-2015_08
Patent number
US09096634B2

Reaction notes

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