Sodium Hydroxide → (2S)-l-Benzyloxymethoxy-2,6-dimethyl-5,6-epoxy-heptane

HRID 493062Notes

Reaction equation

HRID 493062 reaction equation
[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@@H:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=[O:21].[Na+].ClC1C=C(C=CC=1)C(OO)=O.[OH-].[Na+]>C(Cl)Cl.CCOCC.O>[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@@H:12]([CH3:19])[CH2:13][CH2:14][CH:15]1[O:21][C:16]1([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57680469(S)-1-Benzyloxymethoxy-2,6-d imethyl-hept-5-ene

Product 1

HCID 57680482(2S)-l-Benzyloxymethoxy-2,6-dimethyl-5,6-epoxy-heptaneYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Olefin 5 (3.2 g, 12.2 mmol) was dissolved in anhydrous CH2Cl2 (60 mL), and NaHCO3 (1.6 g, 18.4 mmol) was added. Then, 3-chloroperoxybenzoic acid (60%, 12.8 g, 36.6 mmol) was added at room temperature with stirring. The stirring was continued for 24 hours, and the mixture was diluted with ether, and shaken with water and 2M NaOH. The organic layer was washed with water and saturated NH4Cl, dried over Na2SO4, and evaporated. The residue was chromatographed on silica gel using hexane/EtOAc (9:1) as an eluent to give the oily product 6 (2.5 g, 74%).

Workup

  1. washThe organic layer was washed with water and saturated NH4Cl
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-a64153ac96ab4427b119a33b1e7c0f48
Source dataset
uspto-grants-2009_05
Patent number
US07534777B2

Reaction notes

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