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

HRID 610360Notes

Reaction equation

HRID 610360 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2e489223924c41aab8cf97f99903740c
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Reaction notes

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