Methanol → 7-Butyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one

HRID 1819536Notes

Reaction equation

HRID 1819536 reaction equation
C([O:8][C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([CH2:20][CH2:21][CH2:22][CH3:23])=[CH:15][CH:16]=2)[O:11][C:10]=1[C:24]1[CH:29]=[C:28]([O:30]C)[C:27]([O:32]C)=[C:26]([O:34]C)[CH:25]=1)C1C=CC=CC=1.B(Br)(Br)Br.CO.O>ClCCl>[CH2:20]([C:14]1[CH:13]=[C:12]2[C:17]([C:18](=[O:19])[C:9]([OH:8])=[C:10]([C:24]3[CH:29]=[C:28]([OH:30])[C:27]([OH:32])=[C:26]([OH:34])[CH:25]=3)[O:11]2)=[CH:16][CH:15]=1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 578873513-Benzyloxy-7-butyl-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one

Product 1

HCID 578872957-Butyl-3-hydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-oneYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 39d (0.389 g, 1 mmol) in dichloromethane (15 ml) under Ar was added boron tribromide in dichloromethane (1.0M, 5.0 ml, 5 mmol, 4.9 equ). The mixture was then stirred for 18 hours. Methanol (5 ml) was then added. The reaction was heated to reflux for 2 hours, then concentrated in vacuo to give a brown solid. Water (25 ml) was added and the mixture sonicated then extracted into ethyl acetate (3×). The organic layer was washed with brine then dried (MgSO4) and concentrated in vacuo to give 9d (0.302 g, 77%) as a brown solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated in vacuo
  4. customto give a brown solid
  5. customthe mixture sonicated
  6. extractionthen extracted into ethyl acetate (3×)
  7. washThe organic layer was washed with brine
  8. dry with materialthen dried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ee6d7c2dfbd4dd4bba1bc6ebb45e58d
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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