Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate → Diethyl 3-oxocyclobutane-1,1-dicarboxylate

HRID 1497908Notes

Reaction equation

HRID 1497908 reaction equation
[OH:1][CH:2]1[CH2:5][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[O:1]=[C:2]1[CH2:5][C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:3]1

Participants

4

Reactant 2

HCID 14728564Diethyl 3-hydroxycyclobutane-1,1-dicarboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 14728565Diethyl 3-oxocyclobutane-1,1-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 3-hydroxycyclobutane-1,1-dicarboxylate (159) (649 mg, 3 mmol) in DCM (7 mL) was added PCC (1.37 g, 6.3 mmol) and the mixture was stirred for 4 hours at room temperature. The product was filtered through a silica gel plug and the residue was purified using column chromatography with hexanes/ethyl acetate as eluent to yield diethyl 3-oxocyclobutane-1,1-dicarboxylate (160). 1H NMR (400 MHz, CD2Cl2) δ 4.28 (q, J=7.2 Hz, 4H), 3.63 (s, 4H), 1.31 (t, J=7.2 Hz, 6H). MS m/z 215.1 (M+1)+.

Workup

  1. filtrationThe product was filtered through a silica gel plug
  2. customthe residue was purified

Sources & evidence

ORD record
ord-04ca271fe25f4f56af7bd2d77fe41fae
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

Loading…