Tetrahydrofuran → 6-Benzyloxy-3-(3-(methoxycarbonyl)benzylidene)-4-chromanone

HRID 610360ノート

反応式

HRID 610360 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH2:14][CH2:13][C:12]2=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O)([O:22][CH3:23])=[O:21].N1CCCC1.O1CCCC1>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH2:14][C:13](=[CH:27][C:26]1[CH:29]=[CH:30][CH:31]=[C:24]([C:20]([O:22][CH3:23])=[O:21])[CH:25]=1)[C:12]2=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 31268PyrrolidineHCID 639145Methyl 3-formylbenzoateHCID 144227766-(Benzyloxy)chroman-4-one

生成物 1

HCID 545635856-Benzyloxy-3-(3-(methoxycarbonyl)benzylidene)-4-chromanone収率 64.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 17 g of 6-benzyloxy-4-chromanone, 11.3 g of 3-carbomethoxybenzaldehyde, 14.4 g of pyrrolidine, 100 ml of tetrahydrofuran and 300 ml of methanol was stirred at room temperature overnight. The volatiles were evaporated in vacuo to afford the crude product, which was purified by column chromatography on silica gel eluting with dichloromethane. The product fractions were combined and concentrated to an oil which crystallized upon trituration with methanol to give 17.2 g of title product, m.p. 109-112° C.

後処理

  1. customThe volatiles were evaporated in vacuo
  2. customto afford the crude product, which
  3. customwas purified by column chromatography on silica gel eluting with dichloromethane
  4. concentrationconcentrated to an oil which
  5. customcrystallized upon trituration with methanol

出典と根拠

ORDレコード
ord-2e489223924c41aab8cf97f99903740c
出典データセット
uspto-grants-1999_12
特許番号
US05998451

反応ノート

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