Water → HCID 58805151, compound

HRID 349708Notes

Reaction equation

HRID 349708 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([OH:14])[C:3]=1[C:15](=[O:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].[C:24](Cl)(=O)[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.O>CC(C)=O>[OH:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]2[C:3]=1[C:15](=[O:17])[CH:16]=[C:24]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[O:14]2

Participants

6

Reactant 4

HCID 962Water2×HCID 7477p-Anisoyl chlorideHCID 11430Potassium CarbonateHCID 58805171HCID 58805171, compound

Product 1

HCID 58805151HCID 58805151, compoundYield 5.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 1-(2,6-dihydroxy-4-morpholin-4-yl-phenyl)-ethanone (112 mg, 0.472 mmol) and K2CO3 (326 mg, 2.36 mmol) in acetone (3 mL) was added p-anisoyl chloride (0.066 mL, 0.472 mmol). The reaction vessel was sealed and heated to 80° C. for 4 days. After cooling to room temperature, water (about 2 mL) was added, and the mixture was allowed to stir for about 15 min. The contents were transferred to a separatory funnel containing water (5 mL) and extracted with EtOAc (3×15 mL). The organic layer was dried (MgSO4) and concentrated. The concentrate was purified via Biotage chromatography with gradient elution from 100% hexanes to 30% EtOAc/hexanes to yield 9 mg (5%) of 5-hydroxy-2-(4-methoxy-phenyl)-7-morpholin-4-yl-chromen-4-one. Me is CH3—.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling to room temperature
  3. customThe contents were transferred to a separatory funnel
  4. extractionextracted with EtOAc (3×15 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe concentrate was purified via Biotage chromatography with gradient elution from 100% hexanes to 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-b96608b6fc21479ba4136fb52c83cb38
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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