1-Penten-3-one → 2-(2-Hydroxyethyl)-5-methoxy-2-(3-oxopentyl)-1-indanone

HRID 7901

반응식

HRID 7901 반응식
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:15].[CH:16]([C:18]([CH2:20][CH3:21])=[O:19])=[CH2:17].C[O-].[Na+]>CO.CCOC(C)=O>[OH:1][CH2:2][CH2:3][C:4]1([CH2:17][CH2:16][C:18](=[O:19])[CH2:20][CH3:21])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:13][CH3:14])[CH:10]=2)[C:5]1=[O:15]

참가 물질

6

반응물 3

HCID 153941-Penten-3-oneHCID 10942334Sodium MethoxideHCID 219908562-(2-Hydroxyethyl)-5-methoxy-1-indanone

생성물 1

HCID 219909372-(2-Hydroxyethyl)-5-methoxy-2-(3-oxopentyl)-1-indanone수율 93%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A solution of 2-(2-hydroxyethyl)-5-methoxy-1-indanone (105 mg, 0.51 mmol) in methanol (2.0 mL) at room temperature was treated with ethyl vinyl ketone (EVK, 0.102 mL) and 0.5M sodium methoxide in methanol (0.204 mL, 0.1 mmol). The mixture was stirred in a capped flask and heated in an oil bath at 60° C. for 8 hours. After cooling, the reaction mixture was diluted with EtOAc (25 mL), washed with 0.2N HCl (15 mL), water (15 mL), and brine (15 mL), dried over MgSO4, filtered, and evaporated under vacuum to afford 2-(2-hydroxyethyl)-5-methoxy-2-(3-oxopentyl)-1-indanone (138 mg, 93% yield) as an oil.

후처리

  1. temperatureAfter cooling
  2. washwashed with 0.2N HCl (15 mL), water (15 mL), and brine (15 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-787cbd4a712c4b168df30fdb5fe09b66
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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