Sodium hydride → ethyl (E) 6-(4-methoxyethoxymethoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-(dimethylphosphono)-4-methyl-4-hexenoate

HRID 1781540

反応式

HRID 1781540 の反応式
[CH3:1][O:2][P:3]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])([O:5][CH3:6])=[O:4].[H-].[Na+].[CH3:15][O:16][C:17]1[C:25]([CH3:26])=[C:24]2[C:20]([C:21](=[O:27])[O:22][CH2:23]2)=[C:19]([O:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH3:34])[C:18]=1[CH2:35]/[CH:36]=[C:37](\[CH3:40])/[CH2:38]Br>CN(C=O)C>[CH3:34][O:33][CH2:32][CH2:31][O:30][CH2:29][O:28][C:19]1[C:18]([CH2:35]/[CH:36]=[C:37](\[CH3:40])/[CH2:38][CH:7]([P:3]([O:5][CH3:6])([O:2][CH3:1])=[O:4])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:17]([O:16][CH3:15])[C:25]([CH3:26])=[C:24]2[C:20]=1[C:21](=[O:27])[O:22][CH2:23]2

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 67555Ethyl (dimethoxyphosphinoyl)acetateHCID 67019128HCID 67019128、化合物

生成物 1

HCID 131719269ethyl (E) 6-(4-methoxyethoxymethoxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-(dimethylphosphono)-4-methyl-4-hexenoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of ethyl dimethylphosphonoacetate (135 mg) in DMF (5 ml) at 0° was added 50% NaH/oil (33 mg), and the mixture stirred for 10 minutes. (E)-4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy7-methyl -3-oxoisobenzofuran-5-yl)-2-methylbut-2-enyl bromide (600 mg) was added at the same temperature and allowed to reach room temperature in 30 minutes. The reaction was poured onto water and extracted with EtOAc. The organic layers were washed with water, dried over sodium sulfate, and evaporated to give the crude product which was purified by flash chromatography (CH2Cl2 followed by EtOAc) to obtain ethyl (E)-6-(4-methoxyethoxymethoxy -1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-(dimethylphosphono) -4-methyl-4-hexenoate as an oil.

後処理

  1. waitto reach room temperature in 30 minutes
  2. additionThe reaction was poured onto water
  3. extractionextracted with EtOAc
  4. washThe organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto give the crude product which
  8. customwas purified by flash chromatography (CH2Cl2 followed by EtOAc)

出典と根拠

ORDレコード
ord-6b852ad794654a8dae8183b02d827428
出典データセット
uspto-grants-1997_05
特許番号
US05633279

関連ノート

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