Water → (e)-3-[3'-Adamantan-1-yl-4'-(2-methoxyethoxymethoxy)-biphenyl-4-yl]-acrylic acid methyl ester

HRID 41721

反応式

HRID 41721 の反応式
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([C:19]34[CH2:28][CH:23]5[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]5)[CH2:20]3)[CH2:26]4)[CH:13]=2)=[CH:8][CH:7]=1.[H-].[Na+].[CH2:32](Cl)[O:33][CH2:34][CH2:35][O:36][CH3:37].O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])=[C:14]([C:19]34[CH2:28][CH:23]5[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]5)[CH2:20]3)[CH2:26]4)[CH:13]=2)=[CH:10][CH:11]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 10293655(E)-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)-acrylic acid methyl ester

生成物 1

HCID 67401513(e)-3-[3'-Adamantan-1-yl-4'-(2-methoxyethoxymethoxy)-biphenyl-4-yl]-acrylic acid methyl ester収率 84%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of (E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)-acrylic acid methyl ester (120 mg, 0.309 mmol) in 1 ml of anhydrous DMF, was dropped into a 1 ml suspension of NaH (14.8 mg, 0.371 mmol, 60% in mineral oil) in anhydrous DMF (0.3 ml) at 0° C. The resulting red solution was stirred at RT for 30 min, then MEM-Cl (46 mg, 0.371 mmol) was added. After stirring overnight at RT, iced water was added and the mixture was extracted several times with EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated under vacuo. The resulting crude product was purified on silica gel (acetone:hexane 15:85) to obtain (E)-3-[3′-adamantan-1-yl-4′-(2-methoxyethoxymethoxy)-biphenyl-4-yl]-acrylic acid methyl ester (123 mg, 84%).

後処理

  1. stirringAfter stirring overnight at RT
  2. extractionthe mixture was extracted several times with EtOAc
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuo
  6. customThe resulting crude product was purified on silica gel (acetone:hexane 15:85)

出典と根拠

ORDレコード
ord-f9cf0256f72f44759f3049c41035d6eb
出典データセット
uspto-grants-2013_09
特許番号
US08530517B2

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