Methanol → Dimethyl (1R,2S)-3-oxocyclopentane-1,2-dicarboxylate

HRID 1703781Notes

Reaction equation

HRID 1703781 reaction equation
[C:1]([CH2:5][CH:6]([C:13]([O:15][CH3:16])=[O:14])[CH2:7][CH2:8][C:9]([O:11]C)=O)([O:3][CH3:4])=[O:2].CO.C(C(C(OC)=O)(C(OC)=O)CCC)(OC)=O>CC1C=CC(C)=CC=1>[C:1]([C@H:5]1[C@H:6]([C:13]([O:15][CH3:16])=[O:14])[CH2:7][CH2:8][C:9]1=[O:11])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 543737Trimethyl butane-1,2,4-tricarboxylateHCID 12576408HCID 12576408, compound

Product 1

HCID 70256462Dimethyl (1R,2S)-3-oxocyclopentane-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent2×

Procedure

The method of cyclizing 1,2,4-tricarbomethoxy butane, in solution in dry p-xylene containing a trace of methanol, with excess of a suspension in dry p-xylene of a dispersion of an alkali metal hydride in mineral oil, the tricarbomethoxybutane being added portionwise to the alkali metal hydride suspension with mixing at a reaction temperature of about 20° to about 40° C. for a time sufficient to form trans-2,3-dicarbomethoxycyclopentanone.

Workup

  1. additionwith mixing at a reaction temperature of about 20° to about 40° C. for a time sufficient

Sources & evidence

ORD record
ord-badb2d26f6ef4945ada43423442580e4
Source dataset
uspto-grants-1978_11
Patent number
US04125556

Reaction notes

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