Methanol → Dimethyl 2-formylcyclopropane-1,1-dicarboxylate

HRID 372214

Reaction equation

HRID 372214 reaction equation
[CH:1]([CH:3]1[CH2:5][C:4]1([C:11]([O:13][CH2:14]C)=[O:12])[C:6]([O:8][CH2:9]C)=[O:7])=[O:2].C(C=C)=O.COC(=O)C(Br)C(OC)=O.CO>C(O)C>[CH:1]([CH:3]1[CH2:5][C:4]1([C:6]([O:8][CH3:9])=[O:7])[C:11]([O:13][CH3:14])=[O:12])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 7847AcroleinHCID 70087Dimethyl bromomalonateHCID 5337391,1-Diethyl 2-formylcyclopropane-1,1-dicarboxylate

Product 1

HCID 10899359Dimethyl 2-formylcyclopropane-1,1-dicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

By following the procedure of D. T. Warner, cited above, used for preparing diethyl 2-formylcyclopropane-1,1-dicarboxylate from acrolein but using equivalent amount of dimethylbromomalonate and methanol instead of diethylbromomalonate and ethanol, respectively, the title compound, nmr (CDCl3) δ 1.98 (m,2H), 2.80(m, 1H), 3.79(s,6H), 8.82(d, J = 4 cps, 1H), is obtained.

Sources & evidence

ORD record
ord-21ce505f1f0a40418cda96723ae734ff
Source dataset
uspto-grants-1978_05
Patent number
US04089898

Linked notes

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