HCID 20535632, compound → HCID 20535634, compound

HRID 1156226Notes

Reaction equation

HRID 1156226 reaction equation
[CH2:1]([C:4]1[C:13]2[O:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:9](=[O:19])[C:8]=2[C:7]([O:20][CH2:21][CH:22]([OH:24])[CH3:23])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].[H][H]>C(O)C.[Pd]>[OH:24][CH:22]([CH3:23])[CH2:21][O:20][C:7]1[C:8]2[C:9](=[O:19])[CH:10]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:12][C:13]=2[C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 20535632HCID 20535632, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20535634HCID 20535634, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of ethyl 8-allyl-5-(2-hydroxypropoxy)-4-oxo-4H-1-benzopyran-2-carboxylate (1.2 g) in ethanol (50 ml) was added 5% palladium on charcoal (0.2 g). The resulting suspension was then hydrogenated at a pressure of 4 atmospheres. After 30 minutes hydrogen uptake had ceased. The reaction mixture was filtered and the filtrate evaporated in vacuo. The residual solid was crystallised from ethanol giving ethyl 5-(2-hydroxypropoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylate identical in all respects with authentic material.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated in vacuo
  3. customThe residual solid was crystallised from ethanol

Sources & evidence

ORD record
ord-982817680b834adba96cfa3605d50ff1
Source dataset
uspto-grants-1982_06
Patent number
US04335048

Reaction notes

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