Potassium Carbonate → (S)-1-(p-2-isopropoxyethoxymethylphenoxy)-2,3-epoxypropane

HRID 2288260노트

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HRID 2288260 반응식
[CH:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:3])[CH3:2].[F-].[Cs+].C(=O)([O-])[O-].[K+].[K+].[N+](C1C=C(S(O[CH2:37][C@H:38]2[O:40][CH2:39]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C.O>[CH:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:37][C@H:38]2[O:40][CH2:39]2)=[CH:11][CH:10]=1)([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 25953Cesium fluorideHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 102199544-((2-Isopropoxyethoxy)methyl)phenol

생성물 1

HCID 21969460(S)-1-(p-2-isopropoxyethoxymethylphenoxy)-2,3-epoxypropane수율 96.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

p-(2-Isopropoxyethoxy)methylphenol (5 g) was dissolved in DMF (30 ml) under nitrogen atmosphere and the solution was cooled to 0° C. Cesium fluoride (0.72 g) and potassium carbonate (4.27 g) were added thereto, and the mixture was stirred for 1 hour. Then (S)-glycidyl m-nitrobenzenesulfonate (6.16 g, 99.7% e.e.) was added thereto and the mixture was stirred for 24 hours at the same temperature. After the reaction, water was added to the filtrate, the solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/ethyl acetate; 1:1) to give 6.08 g of (S)-1-(p-2-isopropoxyethoxymethylphenoxy)-2,3-epoxypropane (yield 96%, optical purity 99.6% e.e.) as a colorless oil.

후처리

  1. stirringthe mixture was stirred for 24 hours at the same temperature
  2. additionwas added to the filtrate
  3. extractionthe solution was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate, condensed

출처 및 근거

ORD 기록
ord-7318814ed964412b8fcab9e74ef7d2b0
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06087512

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