Sodium Hydroxide → HCID 10559871, compound

HRID 485710Notes

Reaction equation

HRID 485710 reaction equation
[CH3:1][C:2]1([CH3:12])[CH:4]([CH2:5]COC)[CH:3]1[C:9]([O-:11])=[O:10].[OH-:13].[Na+]>CC(C)=O>[CH3:12][C:2]1([CH3:1])[C@H:4]([CH:5]=[O:13])[C@H:3]1[C:9]([O:11][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20269204HCID 20269204, compound

Product 1

HCID 10559871HCID 10559871, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 45.26 g of the product of Step A, 50 ml of 2N sodium hydroxide solution and 450 ml of acetone was stirred for 6 hours at 20° C. and was evaporated to dryness. The residue was added to water and ether and the decanted aqueous phase was extracted with ether. The combined organic phases were evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 4-1 hexane-ethyl acetate mixture yielded 28.75 g of tert.-butyl (1R,trans) 2,2-dimethyl-3-formyl-cyclopropane-carboxylate.

Workup

  1. customwas evaporated to dryness
  2. additionThe residue was added to water and ether
  3. extractionthe decanted aqueous phase was extracted with ether
  4. customThe combined organic phases were evaporated to dryness under reduced pressure
  5. customthe residue was chromatographed over silica gel
  6. washElution with a 4-1 hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-d18e083c1a574b2185a98b6a14863837
Source dataset
uspto-grants-1985_08
Patent number
US04537897

Reaction notes

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