Methyl 3-oxovalerate → Methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate

HRID 2270452노트

반응식

HRID 2270452 반응식
[CH3:1][CH2:2][C:3]1[C:8]2[NH:9][CH:10]=[C:11]([CH2:12][CH2:13][OH:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1.O=[C:16]([CH2:22][CH3:23])[CH2:17][C:18]([O:20][CH3:21])=[O:19]>Cl>[CH2:22]([C:16]1([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:10]2[NH:9][C:8]3[C:7]([C:11]=2[CH2:12][CH2:13][O:14]1)=[CH:6][CH:5]=[CH:4][C:3]=3[CH2:2][CH3:1])[CH3:23]

참가 물질

4

반응물 2

HCID 121699Methyl 3-oxovalerateHCID 1982317-Ethyltryptophol

생성물 1

HCID 527310Methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate수율 79%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
27.5 °C

실험 절차

To a solution of 7-ethyltryptophol (12.0 g) in 1-butanolic hydrogen chloride (5% w/v, 100.0 ml), methyl 3-oxopentanoate (9.1 g) was added in one lot, at 25° C. The reaction mixture was stirred at 25-30° C. for 7 hours. The reaction mixture was extracted with hexane (100.0 ml). Hexane was concentrated to about 20 ml and methanol (10 ml) was added. The product was filtered, washed with methanol and dried to afford the titled compound (14.7 g, 79%), m.p. 128-130° C.; purity: 96.2%.

후처리

  1. extractionThe reaction mixture was extracted with hexane (100.0 ml)
  2. concentrationHexane was concentrated to about 20 ml and methanol (10 ml)
  3. additionwas added
  4. filtrationThe product was filtered
  5. washwashed with methanol
  6. customdried

출처 및 근거

ORD 기록
ord-a2dc2fd1d57d472e8baa07739226bfe8
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06331638B1

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