HCID 20074163, compound → HCID 20074167, compound

HRID 704320Notes

Reaction equation

HRID 704320 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]([OH:14])[CH:8]([CH2:15][C:16]([N:18](C)[CH2:19]C3C=CC(OC)=CC=3)=[O:17])[C:7]=2[CH:29]=1)#[N:2]>O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:12])([CH3:13])[CH:9]([OH:14])[CH:8]([CH2:15][C:16]([NH:18][CH3:19])=[O:17])[C:7]=2[CH:29]=1)#[N:2]

Participants

3

Reactant 1

HCID 20074163HCID 20074163, compound

Product 1

HCID 20074167HCID 20074167, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 6-cyano-3,4-dihydro-3-hydroxy-N-methyl-N-(4-methoxy-benzyl)-2,2-dimethyl-2H-1-benzopyran-4-acetamide (0.5 g) in methanesulpnonic acid (5 ml) was stirred at room temperature for 6 days. Water was added, and the mixture extracted into ethyl acetate. The combined organic layers were washed with sodium bicarbonate solution, brine, then dried (MgSO4), filtered and evaporated. Tne crude product was chromatographed (Si gel, ethyl acetate - pentane gradient elution) to give the title compound, which recrystallised from ethyl acetate as a colourless solid (40 mg) having m.pt. 141°-2° C.

Workup

  1. extractionthe mixture extracted into ethyl acetate
  2. washThe combined organic layers were washed with sodium bicarbonate solution, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customTne crude product was chromatographed
  7. wash(Si gel, ethyl acetate - pentane gradient elution)

Sources & evidence

ORD record
ord-c05bd224d3bf4ba5a8d1cd9911bd5e4d
Source dataset
uspto-grants-1991_01
Patent number
US04987138

Reaction notes

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