HCID 86737893, compound → HCID 21163157, compound

HRID 1278268Notes

Reaction equation

HRID 1278268 reaction equation
[C:1]([C:4]1[CH:36]=[CH:35][C:7]([O:8][CH2:9][CH:10]([OH:34])[CH2:11][O:12][C:13]2[CH:30]=[CH:29][C:16]3[C:17](=[O:28])[CH:18]=[C:19](/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:20][C:15]=3[C:14]=2[CH2:31][CH2:32][CH3:33])=[C:6]([CH2:37][CH2:38][CH3:39])[C:5]=1[OH:40])(=[O:3])[CH3:2]>O1CCOCC1.[Pd]>[C:1]([C:4]1[CH:36]=[CH:35][C:7]([O:8][CH2:9][CH:10]([OH:34])[CH2:11][O:12][C:13]2[CH:30]=[CH:29][C:16]3[C:17](=[O:28])[CH:18]=[C:19]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[O:20][C:15]=3[C:14]=2[CH2:31][CH2:32][CH3:33])=[C:6]([CH2:37][CH2:38][CH3:39])[C:5]=1[OH:40])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86737893HCID 86737893, compound

Product 1

HCID 21163157HCID 21163157, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

trans-Ethyl 3-[7-[3-(4-acetyl-3-hydroxy-2-n-propyl phenoxy)-2-hydroxypropyloxy]-4-oxo-8-n-propyl-4H-1-benzopyran-2-yl]acrylate (1.2 g) in dioxan was hydrogenated, over a palladium-charcoal catalyst, at atmospheric pressure and ambient temperature. The catalyst was removed by filtration and the concentrated filtrate chromatographed over silica-gel (60 g). Elution with ether afforded a white solid which was crystallised from etherpetrol (40°-60°) to yield ethyl 3-[7-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-2-hydroxypropyloxy]-4-oxo-8-n-propyl-4H-1-benzopyran-2-yl]propionate (0.79 g), mp 137°-138° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe concentrated filtrate chromatographed over silica-gel (60 g)
  3. washElution with ether
  4. customafforded a white solid which
  5. customwas crystallised from etherpetrol (40°-60°)

Sources & evidence

ORD record
ord-b57c1fd3fc944ab683f1b82383cc8a6c
Source dataset
uspto-grants-1981_07
Patent number
US04281008

Reaction notes

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