Methanol → HCID 57887306, compound

HRID 1819559Notes

Reaction equation

HRID 1819559 reaction equation
[CH2:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:32])[C:8]([OH:31])=[C:9]([C:13]3[CH:18]=[C:17]([O:19]C)[C:16]([O:21]CC4C=CC=CC=4)=[C:15]([O:29]C)[CH:14]=3)[O:10]2)=[CH:5][C:4]=1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH3:2].B(Br)(Br)Br.CO.O>ClCCl>[CH2:1]([C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:32])[C:8]([OH:31])=[C:9]([C:13]3[CH:14]=[C:15]([OH:29])[C:16]([OH:21])=[C:17]([OH:19])[CH:18]=3)[O:10]2)=[CH:5][C:4]=1[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 57887315HCID 57887315, compound

Product 1

HCID 57887306HCID 57887306, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 7-ethyl-3-hydroxy-6-octyl-2-(4-benzyloxy-3,5-dimethoxy-phenyl)-chromen-4-one 59 (0.125 g, 0.2 mmol) in dichloromethane (10 ml) under Ar at 0° C. was added boron tribromide in dichloromethane (1.0M, 1.2 ml, 1.2 mmol, 5.2 equ). The mixture was warmed to room temperature and then stirred for 21 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 (10 ml) was added then extracted into ethyl acetate (3×). The organic layer was washed with brine then dried (MgSO4) and concentrated in vacuo to give 12 (0.088 g, 100% over 2 steps) as a green solid.

Workup

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

Sources & evidence

ORD record
ord-0003eb8dd2524425a664a7d2c17a2f85
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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