HCID 10539589, compound → HCID 10986992, compound

HRID 376526Notes

Reaction equation

HRID 376526 reaction equation
Br[C:2]1([CH:13]=[O:14])[C@@H:4]([C:5]([O:7][CH3:8])=[O:6])[C@@H:3]1[C:9]([O:11][CH3:12])=[O:10]>[Zn].C(O)(=O)C>[C:9]([C@@H:3]1[CH:2]([CH:13]=[O:14])[C@H:4]1[C:5]([O:7][CH3:8])=[O:6])([O:11][CH3:12])=[O:10]

Participants

4

Reactant 1

HCID 10539589HCID 10539589, compound

Product 1

HCID 10986992HCID 10986992, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of (1R,2R)-3-bromo-1,2-dicarbomethoxy-3-formyl-cyclopropane (428 mg, 1.6 mmmol), zinc powder (230 mg, 3.5 mmol) and acetic acid (2 ml) was stirred at room temperature over a period of 4 hours. Filtration, evaporation and column chromatography yielded (1R,2R)-1,2-dicarbomethoxy-3-formyl-cyclopropane (265 mg, 88%) as a colorless oil. [α]20D=-48° (c=1 in MeOH); 1H NMR (CDCl3): d 2.53 (ddd, J=5, 6, 8 Hz, 1H), 2.71 (dd, J=6, 8 Hz, 1H), 3.01 (t, J=6 Hz, 1H), 3.76 (s, 6H), 9.42 (d, J=5 Hz, 1H); MS (FAB) m/e 187 [M+H+ ].

Workup

  1. filtrationFiltration, evaporation and column chromatography

Sources & evidence

ORD record
ord-2c92d411770b4ba3994183c48d70d15a
Source dataset
uspto-grants-2000_02
Patent number
US06020525

Reaction notes

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