2H-1-BENZOPYRAN-2-ONE, 2-(4-HYDROXYPHENYL)- → HCID 11694272, compound

HRID 884716Notes

Reaction equation

HRID 884716 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:11][C:12]1[CH:28]=[CH:27][C:15]([C:16]2[O:17][C:18]3[C:23]([C:24](=O)[CH:25]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=1>C1COCC1>[O:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:24][CH:25]=[C:16]1[C:15]1[CH:14]=[CH:13][C:12]([OH:11])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 2290162H-1-BENZOPYRAN-2-ONE, 2-(4-HYDROXYPHENYL)-HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 11694272HCID 11694272, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of aluminum chloride (680 mg, 5.1 mmol) in dry THF (50 mL) was cooled to 0° C. under nitrogen. LAH (580 mg, 15.5 mmol) was added to the above solution and the resulting mixture was stirred for 20 min at 0° C., and then at rt for additional 20 min, and cooled down to −50° C. 4′-Hydroxyflavone (400 mg, 1.7 mmol) dissolved in 60 mL of THF was added slowly. The reaction mixture was stirred at −50° C. for 2 h and then for 2 h at rt. The reaction was quenched by careful addition of water (traces, to decompose LiAlH4) and the solvent was removed under reduced pressure. The crude product was initially purified by crystallization from MeOH, and then further purified by column chromatography (silica gel, 5-20% EtOAc/hexane) and repeated crystallization from MeOH to afford 109 mg of 4-(4H-chromen-2-yl)-phenol (29%). MS (ES) m/z: 225.10 (M+1), 149.04.

Workup

  1. waitat rt for additional 20 min
  2. temperaturecooled down to −50° C
  3. additionwas added slowly
  4. stirringThe reaction mixture was stirred at −50° C. for 2 h
  5. waitfor 2 h at rt
  6. customThe reaction was quenched by careful addition of water (traces, to decompose LiAlH4)
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was initially purified by crystallization from MeOH
  9. customfurther purified by column chromatography (silica gel, 5-20% EtOAc/hexane)
  10. customcrystallization from MeOH

Sources & evidence

ORD record
ord-b8468f3f571c40e6a77acfe7a7726ff6
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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