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

HRID 1819560Notes

Reaction equation

HRID 1819560 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][CH:14]=2)[O:9][C:8]=1[C:28]1[CH:33]=[C:32]([O:34]C)[C:31]([O:36]C)=[CH:30][C:29]=1[O:38]C.CO>C(Cl)Cl>[OH:6][C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][C:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][CH:14]=2)[O:9][C:8]=1[C:28]1[CH:33]=[C:32]([OH:34])[C:31]([OH:36])=[CH:30][C:29]=1[OH:38]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 578873417-Decyl-3-methoxy-2-(2,4,5-trimethoxyphenyl)-4H-1-benzopyran-4-one

Product 1

HCID 578873217-Decyl-3-hydroxy-2-(2,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.0 M solution in DCM) (4.0 ml, 4.06 mmol, 5.0 eq) was added slowly to a solution of 69 (392 mg, 0.81 mmol) in dry DCM (3 ml) at 0° C. under argon. The solution was then stirred overnight and then methanol (5 ml) added slowly. The solution was heated under reflux for 30 min. then concentrated under vacuum. Water (20 ml) was added to the residue and the flask placed in a sonic bath for 5 min. The resulting fine precipitate was filtered off and washed with water (10 ml) then freeze dried to give the flavonol as a red/brown amorphous solid (338 mg, 98%). m.p. decomp >90° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 30 min.
  3. concentrationthen concentrated under vacuum
  4. additionWater (20 ml) was added to the residue
  5. waitthe flask placed in a sonic bath for 5 min
  6. filtrationThe resulting fine precipitate was filtered off
  7. washwashed with water (10 ml)
  8. customthen freeze dried

Sources & evidence

ORD record
ord-c003d00761ff4df49055a070e4dce8cd
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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