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

HRID 7901

反応式

HRID 7901 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-787cbd4a712c4b168df30fdb5fe09b66
出典データセット
uspto-grants-2006_08
特許番号
US07087599B2

関連ノート

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