Methanol → 6-Decyl-3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one

HRID 1819557Notes

Reaction equation

HRID 1819557 reaction equation
[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:9]=2)[O:4][C:3]=1[C:23]1[CH:28]=[C:27]([O:29]C)[C:26]([O:31]CC2C=CC=CC=2)=[C:25]([O:39]C)[CH:24]=1.B(Br)(Br)Br.CO.O>ClCCl>[CH2:13]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[O:4][C:3]([C:23]1[CH:28]=[C:27]([OH:29])[C:26]([OH:31])=[C:25]([OH:39])[CH:24]=1)=[C:2]([OH:1])[C:11]2=[O:12])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 25134Boron tribromideHCID 57887348HCID 57887348, compound

Product 1

HCID 578873326-Decyl-3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-oneYield 110%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 3-hydroxy-6-decyl-2-(4-benzyloxy-3,5-dimethoxy-phenyl)-chromen-4-one (0.369 g, 0.7 mmol) in dichloromethane (20 ml) under Ar at 0° C. was added boron tribromide in dichloromethane (1.0M, 3.4 ml, 3.4 mmol, 5 equ). The mixture was warmed to room temperature and then stirred for 15 hours. Methanol (10 ml) was then added. The reaction was heated to reflux for 1 hour, then concentrated in vacuo to give a brown solid. Water (25 ml) was added and then extracted into ethyl acetate (3×). The organic layer was washed with brine then dried (MgSO4) and concentrated in vacuo to give 11g (0.318 g, 110%) as a brown oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 hour
  3. concentrationconcentrated in vacuo
  4. customto give a brown solid
  5. extractionextracted 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-a47d48c5ded34066b9e9f646cc8e3f3d
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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