HCID 53658647, compound → HCID 2801521, compound

HRID 236949Notes

Reaction equation

HRID 236949 reaction equation
[CH2:1]([C:4]1[C:13]2[O:14][C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:16][C:17](=[O:18])[C:12]=2[CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9]2)[CH:2]=[CH2:3].[H][H]>C(O)C.[Pd]>[O:18]=[C:17]1[CH:16]=[C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[O:14][C:13]2[C:4]([CH2:1][CH2:2][CH3:3])=[C:5]3[C:10](=[CH:11][C:12]1=2)[CH2:9][CH2:8][CH2:7][CH2:6]3

Participants

5

Reactant 2

HCID 53658647HCID 53658647, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 2801521HCID 2801521, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product of step (a) (20 g), in ethanol (120 ml), was treated with a 5% palladium on charcoal catalyst (100 mg), and shaken in a hydrogen atmosphere at 45 psi for 2 hours at room temperature. The catalyst was subsequently filtered off and the filtrate was evaporated. The residue solidified upon trituration with a little diethyl ether and the solid was twice crystallised from aqueous ethanol to give as white crystals, ethyl 6,7,8,9-tetrahydro-4-oxo-10-propyl-4H-naphtho[2,3-b]pyran-2-carboxylate (10 g), mp 98°-99.5°.

Workup

  1. filtrationThe catalyst was subsequently filtered off
  2. customthe filtrate was evaporated
  3. customthe solid was twice crystallised from aqueous ethanol

Sources & evidence

ORD record
ord-5b12cc3a14434413bf4cf1bdffc6aa59
Source dataset
uspto-grants-1979_06
Patent number
US04159273

Reaction notes

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