Ethanol → HCID 18979221, compound

HRID 2393162Notes

Reaction equation

HRID 2393162 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([CH:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:3]=1.C(O)C>[Pd].C(N(CC)CC)C>[OH:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[CH:3][C:4]=1[CH:13]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 2

HCID 702EthanolHCID 18979158HCID 18979158, compound

Product 1

HCID 18979221HCID 18979221, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

Using ethyl 7-(4-chloro-1-hydroxy-2-naphthyl)-7-phenylheptanoate (4.3 g), 10% palladium-on-carbon (0.4 g), ethanol (90 ml), and triethylamine (10 ml), a catalytic hydrogenation reaction was carried out at 50° C. and atmospheric pressure for 16 hours. The reaction mixture was then filtered and the filtrate was concentrated and applied to a silica gel column (hexane-ethyl acetate) to provide the title compound (3.65 g).

Workup

  1. customa catalytic hydrogenation reaction
  2. customwas carried out at 50° C.
  3. filtrationThe reaction mixture was then filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9e1c47d3b4fc4ef9969f7b05c8c251bb
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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