Diethyl Ether → Acetate hexane

HRID 579850Notes

Reaction equation

HRID 579850 reaction equation
[CH3:1][CH2:2][C:3]([O-:6])([CH3:5])[CH3:4].[Na+].CC[O:10][CH2:11][CH3:12]>C1C=CC=CC=1.O1CCCC1>[C:3]([O-:6])(=[O:10])[CH3:5].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 2733478Sodium 2-methylbutan-2-olate

Product 1

HCID 22139250Acetate hexaneYield 95%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.38 ml of a 1.5M solution of sodium tert-amylate in benzene is added to 126 mg of the mesylate lactone obtained at stage A in 2 ml of anhydrous tetrahydrofuran, at 0° C. The temperature is allowed to rise to 20° C. over 15 minutes. After hydrolysis, extraction is done with ether, then the organic phase is washed with salt water. After chromatographing on a silica column (eluent acetate-hexane 40/60), 73 mg of the cis-cyclopropane lactone expected is obtained.

Workup

  1. customAfter hydrolysis, extraction
  2. washthe organic phase is washed with salt water

Sources & evidence

ORD record
ord-69210d36addf4ca3991acae7a751dffe
Source dataset
uspto-grants-1988_06
Patent number
US04749797

Reaction notes

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