Hydrogen Peroxide → HCID 20072998, compound

HRID 704642Notes

Reaction equation

HRID 704642 reaction equation
[CH2:1]=[C:2]1[CH:4]([CH2:5][O:6][C:7](=[O:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:3]1[CH2:15][O:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-:25].[Na+].OO>O1CCCC1.C(OCC)(=O)C>[OH:25][CH2:1][CH:2]1[CH:3]([CH2:15][O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:4]1[CH2:5][O:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 18316998HCID 18316998, compound

Product 1

HCID 20072998HCID 20072998, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 8.36 g (26 mmol) of 3-Methylene-1,2-bis(benzoyloxymethyl)cyclopropane (from Step C) in tetrahydrofuran (THF) was cooled in an ice-water bath. To this solution was added 26 mL (26 mmol) of a 1 M THF solution of borane-THF complex, and the resultant solution was stirred at 5° C. for 2 h. 3N Sodium hydroxide solution (8.67 mL, 26 mmol) was then added slowly to the reaction mixture at 5° C., followed by 7.8 mL (78 mmol) of 30% aqueous hydrogen peroxide solution. The reaction mixture was stirred for 20 min at 5° C., allowed to warm to ambient temperature and stirred for 30 min at ambient temperature. The reaction mixture was diluted with ethyl acetate, washed 3 times with brine (until the pH of the aqueous layer was approximately 7) and concentrated in vacuo. The residue was purified by column chromatography on a 3×65 cm silica gel column eluted with 2% methanol in chloroform. Fractions numbered 35-47 were combined and concentrated in vacuo to give 4.1 g (46% yield) of 3-Hydroxymethyl-1,2-bis((benzoyl)oxymethyl)cyclopropane. DCI NH3MS, M/Z: 341 (M+H)+, 358 (M+NH4)+.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 30 min at ambient temperature
  3. washwashed 3 times with brine (until the pH of the aqueous layer
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on a 3×65 cm silica gel column
  6. washeluted with 2% methanol in chloroform
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9b69f79b5a2423d9e5135b4e80fcf4f
Source dataset
uspto-grants-1991_01
Patent number
US04988703

Reaction notes

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