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

HRID 2270452ノート

反応式

HRID 2270452 の反応式
[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]

参加物

4

反応物 2

HCID 121699Methyl 3-oxovalerateHCID 1982317-Ethyltryptophol

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
27.5 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-a2dc2fd1d57d472e8baa07739226bfe8
出典データセット
uspto-grants-2001_12
特許番号
US06331638B1

反応ノート

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