Hexane → Ethyl 4-[1-(2,2-dimethoxyethyl)-2-{1(tol-4-yl)3,4-dihydro-4,4-dimethyl-naphthalen-7-yl}-(E)-ethenyl]-benzoate

HRID 2606

反応式

HRID 2606 の反応式
C(OP([C:9]([O:25][CH3:26])([O:23][CH3:24])[CH2:10][CH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=1)(OCC)=O)C.[Li]CCCC.CCCCCC.[C:38]1([CH3:58])[CH:43]=[CH:42][C:41]([C:44]2[C:53]3[C:48](=[CH:49][CH:50]=[C:51]([CH:54]=O)[CH:52]=3)[C:47]([CH3:57])([CH3:56])[CH2:46][CH:45]=2)=[CH:40][CH:39]=1>C1COCC1>[CH3:26][O:25][CH:9]([O:23][CH3:24])[CH2:10]/[C:11](/[C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][CH:22]=1)=[CH:54]\[C:51]1[CH:52]=[C:53]2[C:48]([C:47]([CH3:57])([CH3:56])[CH2:46][CH:45]=[C:44]2[C:41]2[CH:40]=[CH:39][C:38]([CH3:58])=[CH:43][CH:42]=2)=[CH:49][CH:50]=1

参加物

6

反応物 4

HCID 8058HexaneHCID 57037360Ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoateHCID 865886771-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde2 回HCID 178418339Butyllithium

生成物 1

HCID 86588679Ethyl 4-[1-(2,2-dimethoxyethyl)-2-{1(tol-4-yl)3,4-dihydro-4,4-dimethyl-naphthalen-7-yl}-(E)-ethenyl]-benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 350 mg, 0.9 mmol, available in accordance with EPO Application No. 0 210 929 published on Feb. 4, 1987), in THF (9 mL), was added n-BuLi in hexane (1.6M solution, 0.7 mL, 1.1 mmol). The mixture was stirred for 1.5 hours. To this solution 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde (Compound C, 200 mg, 0.72 mmol), in THF (1 mL) was added and the mixture was gradually warmed to ambient temperature (4 h). The reaction was quenched by adding water (5 mL), and extracted with ethyl acetate (3×25 mL). The organic layer was washed with brine (10 mL), dried with MgSO4 and the solvent was removed by distillation. The crude material was purified by silicagel chromatography to afford the title compound as a colorless off.

後処理

  1. customThe reaction was quenched
  2. additionby adding water (5 mL)
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried with MgSO4
  6. customthe solvent was removed by distillation
  7. customThe crude material was purified by silicagel chromatography

出典と根拠

ORDレコード
ord-1b0e8d298ae64c8b9df10e43febd3af1
出典データセット
uspto-grants-1998_03
特許番号
US05728846

関連ノート

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