Hydrochloric Acid → HCID 86199579, compound

HRID 1637802Notes

Reaction equation

HRID 1637802 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.C([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:32][CH3:33])=[CH:29][CH:30]=3)[O:25][C:24](=O)[C:23]=2[C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)=[CH:18][CH:17]=1)(=O)C.Cl>O.C(OCC)(=O)C>[F:41][C:38]1[CH:39]=[CH:40][C:35]([C:23]2[CH2:24][O:25][C:26]3[C:31]([C:22]=2[C:19]2[CH:20]=[CH:21][C:16]([OH:15])=[CH:17][CH:18]=2)=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=3)=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18355513HCID 18355513, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86199579HCID 86199579, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium aluminium hydride (0.76 g, 20.03 mmol) was added in small portions to a stirred tetrahydrofuran (150 ml) solution of 4-(4-acetoxyphenyl)-3-(4-fluorophenyl)-7-methoxy-coumarin (4.04 g, 9.99 mmol). After complete addition, the mixture was stirred at room temperature for 30 min., then treated dropwise with 6M hydrochloric acid (30 ml). The resulting mixture was heated to 60-65° C. for 3 h, cooled and diluted with water (100 ml) and ethyl acetate (50 ml). The aqueous layer was separated and further extracted with ethyl acetate (3×100 ml). The combined organic solutions were washed with saturated aqueous sodium chloride, dried over sodium sulfate and evaporated to give an orange solid. This was recrystallised from ethanol/water (75 ml, 4:1) to give the first crop of solid product as colourless needles. The mother liquors were evaporated to give an orange gum, which was subjected to a second aqueous ethanol recrystallisation to give a second crop of colourless needles. The solids were combined and vacuum dried.

Workup

  1. additionAfter complete addition
  2. temperatureThe resulting mixture was heated to 60-65° C. for 3 h
  3. temperaturecooled
  4. customThe aqueous layer was separated
  5. extractionfurther extracted with ethyl acetate (3×100 ml)
  6. washThe combined organic solutions were washed with saturated aqueous sodium chloride
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto give an orange solid
  10. customThis was recrystallised from ethanol/water (75 ml, 4:1)
  11. customto give the first crop of solid product as colourless needles
  12. customThe mother liquors were evaporated
  13. customto give an orange gum, which
  14. customwas subjected to a second aqueous ethanol recrystallisation
  15. customto give a second crop of colourless needles
  16. customvacuum dried

Sources & evidence

ORD record
ord-32d707c1a2794bcabc6c2163bfd23e26
Source dataset
uspto-grants-2000_03
Patent number
US06043269

Reaction notes

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