Methanol → Methyl 3-oxocyclobutane-1-carboxylate

HRID 1852422Notes

Reaction equation

HRID 1852422 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.CO.Cl.[CH2:12](N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([O:8][CH3:12])=[O:7])[CH2:3]1

Participants

6

Reactant 3

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 13992367Methyl 3-oxocyclobutane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

3-Oxocyclobutanecarboxylic acid 1 (350 g, 3.06 mol), methanol (190 mL, 4.69 mol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (885 g, 4.69 mol), 4-dimethylaminopyridine (37 g, 0.30 mol) and dichloromethane (6 L) were stirred at ambient temperature for 24 hours. After the completion of the reaction, it was taken in a separating funnel and washed with 1.5 N HCl solution (1 L), water (2 L×2) and brine (1 L×2). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was taken to the next step without further purification. 1H NMR (300 MHz, CDCl3): δ 3.23-3.25 (m, 2H), 3.27-3.32 (m, 2H), 3.33-3.42 (m, 1H), 3.76 (s, 3H). GC-MS: [M]+ m/z=128.

Workup

  1. customAfter the completion of the reaction, it
  2. customwas taken in a separating funnel
  3. washwashed with 1.5 N HCl solution (1 L), water (2 L×2) and brine (1 L×2)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was taken to the next step without further purification

Sources & evidence

ORD record
ord-c1fdc09a49f84783ae3fbb5a95851679
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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