Water → (Z)-5-Acetylamino-2,4,6,7-tetramethyl-2-styryl-2,3-dihydrobenzofuran

HRID 234255

反応式

HRID 234255 の反応式
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:7]([Li])CCC.[C:12]([NH:15][C:16]1[C:17]([CH3:30])=[C:18]([CH3:29])[C:19]2[O:23][C:22]([CH:25]=O)([CH3:24])[CH2:21][C:20]=2[C:27]=1[CH3:28])(=[O:14])[CH3:13].O>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:12]([NH:15][C:16]1[C:17]([CH3:30])=[C:18]([CH3:29])[C:19]2[O:23][C:22]([CH3:24])(/[CH:25]=[CH:7]\[C:3]3[CH:2]=[CH:1][CH:6]=[CH:5][CH:4]=3)[CH2:21][C:20]=2[C:27]=1[CH3:28])(=[O:14])[CH3:13]

参加物

6

反応物 3

HCID 962WaterHCID 19078578HCID 19078578、化合物HCID 178418244HCID 178418244、化合物

生成物 1

HCID 67671450(Z)-5-Acetylamino-2,4,6,7-tetramethyl-2-styryl-2,3-dihydrobenzofuran収率 77.2%

試薬・触媒・溶媒 2

HCID 70671Benzyltriphenylphosphonium chloride触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-20 °C

実験手順

A suspension of benzyltriphenylphosphonium chloride (0.7 g, 1.8 mmol) in tetrahydrofuran (10 ml) was cooled to -20° C. and n-butyllithium hexane solution (1.6M, 1.12 ml, 1.8 mmol) was added dropwise. The reaction mixture was stirred for 30 minutes and then a solution of 5-acetylamino-2-formyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (0.45 g, 1.7 mmol) in tetrahydrofuran (5 ml) was added. The reaction mixture was stirred at room temperature for additional 30 minutes. Water was added to the reaction mixture and the product was extracted with ethyl acetate. The extract was washed with water, dried and then concentrated. The residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 1:1) to obtain the desired compound (0.44 g, yield: 76.2%) as oil.

後処理

  1. stirringThe reaction mixture was stirred at room temperature for additional 30 minutes
  2. extractionthe product was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 1:1)

出典と根拠

ORDレコード
ord-58df597f495940dda9f2b60e6efab7b3
出典データセット
uspto-grants-1997_01
特許番号
US05594154

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