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

HRID 2352405노트

반응식

HRID 2352405 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

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 dimethyformamide 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).

후처리

  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

출처 및 근거

ORD 기록
ord-3ef3cb22500c4566a4c9f787a99539b7
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04876367

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