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

HRID 234255

반응식

HRID 234255 반응식
[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]

참가 물질

6

반응물 3

HCID 962WaterHCID 19078578HCID 19078578, 화합물HCID 178418244HCID 178418244, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 70671Benzyltriphenylphosphonium chloride촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-20 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-58df597f495940dda9f2b60e6efab7b3
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05594154

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