m-Chloroperbenzoic acid → HCID 54469068, compound

HRID 1740543Notes

Reaction equation

HRID 1740543 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][C:15](=[O:27])/[CH:16]=[CH:17]/[CH2:18][C@@H:19]([CH3:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH3:13]>C(Cl)Cl>[CH2:12]([O:14][C:15](=[O:27])[CH:16]=[CH:17][CH2:18][C@H:19]([CH3:26])[CH2:20][CH2:21][CH:22]1[C:23]([CH3:25])([CH3:24])[O:9]1)[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86754652HCID 86754652, compound

Product 1

HCID 54469068HCID 54469068, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

13.54 g of 3-chloro-perbenzoic acid (MCPBA, 70%) was dissolved in 30 ml of CH2Cl2 and cooled to 0°. 8.84 g of (E)-(S)-5,9-dimethyl-deca-2,8-dienoic acid ethyl ester dissolved in 15 ml of CH2Cl2, was slowly added and the mixture kept for an additional 0.5 h in the ice bath. The reaction was then quenched by pouring onto crushed ice/sodium pyrosulfite, extracted twice with AcOEt, washed with 2N NaOH, water and brine, dried over sodium sulfate and evaporated to dryness to yield 9.59 g of (5R)-7-((RS)-3,3-dimethyl-oxiranyl)-5-methyl-hept-2-enoic acid ethyl ester as 1/1 epimeric mixture, sufficiently pure for the next step.

Workup

  1. temperaturecooled to 0°
  2. additionwas slowly added
  3. customThe reaction was then quenched
  4. additionby pouring
  5. customonto crushed ice/sodium pyrosulfite
  6. extractionextracted twice with AcOEt
  7. washwashed with 2N NaOH, water and brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-3422fde44bf444ca9509a6f406138495
Source dataset
uspto-grants-1999_10
Patent number
US05969190

Reaction notes

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