Methanol → HCID 11830739, compound

HRID 1033961Notes

Reaction equation

HRID 1033961 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][C:5]1([CH3:18])[C@@H:7]([CH:8](Br)[C:9](=O)[CH2:10]Br)[C@H:6]1[C:14]([O:16][CH3:17])=[O:15].C[OH:20]>>[CH3:4][C:5]1([CH3:18])[C@@H:7](/[CH:8]=[CH:9]\[C:10]([O:2][CH3:1])=[O:20])[C@H:6]1[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 10936779HCID 10936779, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 11830739HCID 11830739, compound

Conditions

Temperature
0 °C

Procedure

0.16 g of sodium methylate and 1.6 ml of methanol were mixed together under an inert gas atmosphere and after the mixture was cooled to about 0° C., 0.5 g of methyl (1R,cis) 2,2-dimethyl-3-(1,3-dibromo-2-oxopropyl)-cyclopropane-1-carboxylate in solution in 2.5 ml of methanol were slowly added. The mixture was stirred at about -5° C. for 90 minutes and then the solvent was evaporated under reduced pressure at about 30° C. and 10 ml of methylene chloride were added. The solution was washed with water, dried and concentrated to dryness to obtain 0.324 g of crude product which was chromatographed on silica, eluting with a cyclohexane - ethyl acetate mixture (6-4) to obtain 0.262 g of the expected product.

Workup

  1. customthe solvent was evaporated under reduced pressure at about 30° C.
  2. addition10 ml of methylene chloride were added
  3. washThe solution was washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customto obtain 0.324 g of crude product which
  7. customwas chromatographed on silica
  8. washeluting with a cyclohexane - ethyl acetate mixture (6-4)

Sources & evidence

ORD record
ord-08a3fc4c023841939f90429bd8a2b260
Source dataset
uspto-grants-1994_05
Patent number
US05312964

Reaction notes

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