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

HRID 493062노트

반응식

HRID 493062 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a64153ac96ab4427b119a33b1e7c0f48
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534777B2

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