HCID 53968416, compound → HCID 54077037, compound

HRID 327991Notes

Reaction equation

HRID 327991 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)=[C:11]([CH:28]=[O:29])[CH:10]=1)[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)=[C:11]([CH:28]=[O:29])[CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 53968416HCID 53968416, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54077037HCID 54077037, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 1.2 g (2.88 mmol) sample of rac-4-[3-formyl-4-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexyn-1-yl]phenoxy]butanoic acid ethyl ester from example 49 was hydrogenated in ethyl acetate using 80 mg of 10% palladium on carbon, at room temperature, under 1 atmosphere of hydrogen. When the reduction was complete, the catalyst was filtered with suction and the filtrate concentrated under reduced pressure giving rac-4-[3-formyl-4-[6-[(tetrahydro-2H-pyran-2-yl)oxy]hexyl]phenoxy]butanoic acid ethyl ester as a pale-yellow oil, in quantitative yield.

Workup

  1. filtrationthe catalyst was filtered with suction
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-504f89c171e34a3c88b114a7d053513c
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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