Diethyl Ether → 5-(3,3-Dimethylbutanoyl)-3-methyl-1,2-di(2-[2-(2-tetrahydropyranyloxy)ethoxy]ethoxy)benzene

HRID 867985ノート

反応式

HRID 867985 の反応式
[CH3:1][C:2]1[CH:8]=[C:7]([C:9](=[O:15])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[C:4]([OH:5])[C:3]=1[OH:16].Cl[CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.[C:30](=[O:33])([O-])[O-:31].[K+].[K+].[CH2:36]([O:38][CH2:39][CH3:40])[CH3:37]>CN(C)C=O.O>[CH3:14][C:11]([CH3:13])([CH3:12])[CH2:10][C:9]([C:7]1[CH:8]=[C:2]([CH3:1])[C:3]([O:16][CH2:37][CH2:36][O:38][CH2:39][CH2:40][O:31][CH:30]2[CH2:4][CH2:3][CH2:2][CH2:1][O:33]2)=[C:4]([O:5][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:6]=1)=[O:15]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 109657372-[2-(2-Chloroethoxy)ethoxy]oxaneHCID 142793123-Methyl-5-(3,3-dimethylbutanoyl)catechol

生成物 1

HCID 146756075-(3,3-Dimethylbutanoyl)-3-methyl-1,2-di(2-[2-(2-tetrahydropyranyloxy)ethoxy]ethoxy)benzene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

A solution of 3-methyl-5-(3,3-dimethylbutanoyl)catechol (12 g, 0.054 mole), 2-(2-[2-chloroethoxy]ethoxy)tetrahydropyran (24.8 g, 0.119 mole) and potassium carbonate (16.6 g, 0.12 mole) in 100 ml dimethylformamide was stirred under a nitrogen atmosphere at 140° C. for 16 hours. The reaction mixture was cooled to 25° C. and 500 ml diethyl ether and 300 ml water were added. The layers were separated and the organic layer was washed with four 250 ml portions of water and 100 ml brine, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The resulting brown oil was purified by column chromatography over silica gel with 10% ethyl acetate--90% chloroform. The title compound was isolated as a yellow oil (13.5 g, 44% yield).

後処理

  1. customThe layers were separated
  2. washthe organic layer was washed with four 250 ml portions of water and 100 ml brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent evaporated in vacuo
  5. customThe resulting brown oil was purified by column chromatography over silica gel with 10% ethyl acetate--90% chloroform

出典と根拠

ORDレコード
ord-4cbe639b0b834f0fbe4d477b38d91685
出典データセット
uspto-grants-1988_10
特許番号
US04777270

反応ノート

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