Tetrahydrofuran → Ethyl 10-(6-bromo-2,3,4,5-tetramethoxyphenyl)-9,9-diethoxycarbonyldecanoate

HRID 2268441ノート

反応式

HRID 2268441 の反応式
C1COCC1.[CH2:6]([O:8][C:9]([CH:11]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[CH3:7].[H-].[Na+].[Br:31][C:32]1[C:37]([CH2:38]Br)=[C:36]([O:40][CH3:41])[C:35]([O:42][CH3:43])=[C:34]([O:44][CH3:45])[C:33]=1[O:46][CH3:47]>[Cl-].[NH4+]>[Br:31][C:32]1[C:37]([CH2:38][C:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:36]([O:40][CH3:41])[C:35]([O:42][CH3:43])=[C:34]([O:44][CH3:45])[C:33]=1[O:46][CH3:47]

参加物

6

反応物 4

HCID 8028Tetrahydrofuran3 回HCID 24758Sodium hydrideHCID 183486201-Bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzeneHCID 18348648Ethyl 2,9-diethoxycarbonylnonanoate

生成物 1

HCID 18348563Ethyl 10-(6-bromo-2,3,4,5-tetramethoxyphenyl)-9,9-diethoxycarbonyldecanoate収率 65.6%

試薬・触媒・溶媒 1

HCID 25517Ammonium Chloride溶媒

実験手順

A THF (10 ml) solution of ethyl 2,9-diethoxycarbonylnonanoate (8.86 g, 26.8 mmols) was dropwise added to a THF (90 ml) suspension of sodium hydride (60% oily, 1.29 g, 32.2 mmols) at room temperature. The reaction mixture was stirred for 2 hours, and then a THF (10 ml) solution of 1-bromo-6-bromomethyl-2,3,4,5-tetramethoxybenzene (10.9 g, 29.5 mmols) was dropwise added at room temperature, and stirring was continued for additional 2 hours. The reaction mixture was diluted with a saturated aqueous ammonium chloride solution and then concentrated in vacuo. The residue was extracted with ethyl acetate, and the resulting organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated in vacuo. The crude product thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 4:1) to obtain the entitled compound (10.9 g) as an oil.

後処理

  1. stirringstirring
  2. waitwas continued for additional 2 hours
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe resulting organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, then dried
  7. concentrationconcentrated in vacuo
  8. customThe crude product thus obtained
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 4:1)

出典と根拠

ORDレコード
ord-c4c97b25ee6b480188671156d1539fe8
出典データセット
uspto-grants-2001_12
特許番号
US06326369B1

反応ノート

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