Methanol → 7-Ethyl-3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one

HRID 1819531Notes

Reaction equation

HRID 1819531 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:26])[C:8]([OH:25])=[C:9]([C:13]3[CH:18]=[C:17]([O:19]C)[C:16]([O:21]C)=[C:15]([O:23]C)[CH:14]=3)[O:10]2)=[CH:5][CH:4]=1)[CH3:2].B(Br)(Br)Br.CO.O>ClCCl>[CH2:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:26])[C:8]([OH:25])=[C:9]([C:13]3[CH:14]=[C:15]([OH:23])[C:16]([OH:21])=[C:17]([OH:19])[CH:18]=3)[O:10]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 578873437-Ethyl-3-hydroxy-2-(3,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one

Product 1

HCID 248026257-Ethyl-3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 26 (0.504 g, 1.4.mmol) in dichloromethane (50 ml) under Ar at 0° C. was added boron tribromide in dichloromethane (1.0M, 10 ml, 10 mmol, 7 equ). The mixture was warmed to room temperature and then stirred for 21 hours. The reaction was then cooled to 10° C. and methanol (10 ml) added. The reaction was heated to reflux for 3 hours, then concentrated in vacuo to give an orange solid. Water (50 ml) was added and stirred for two hours then left to stand overnight then 9c (0.313 g, 70%) was collected as a black solid.

Workup

  1. temperatureThe reaction was then cooled to 10° C.
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 3 hours
  4. concentrationconcentrated in vacuo
  5. customto give an orange solid
  6. stirringstirred for two hours
  7. waitthen left
  8. waitto stand overnight
  9. custom9c (0.313 g, 70%) was collected as a black solid

Sources & evidence

ORD record
ord-8736e00657a84f63a778dcc3773b2b9b
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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