HCID 86642715, compound → HCID 86642716, compound

HRID 1361095Notes

Reaction equation

HRID 1361095 reaction equation
C([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][S:25]([CH2:28][CH2:29][CH2:30][CH3:31])(=[O:27])=[O:26])=[C:20]([O:32][CH3:33])[CH:19]=2)[CH:12]=[CH:11][C:10]=1/[CH:34]=[CH:35]/[C:36]([O:38][CH3:39])=[O:37])C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH2:28]([S:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][CH2:15][C:13]2[CH:12]=[CH:11][C:10]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[C:9]([OH:8])[CH:14]=2)=[CH:19][C:20]=1[O:32][CH3:33])(=[O:27])=[O:26])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 2

HCID 86642715HCID 86642715, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86642716HCID 86642716, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

78 mg (10% mass equivalent) of 10% palladium-on-charcoal are added to a solution of 780 mg (1.4 mmol) of methyl(E)-3-(2-benzyloxy-4-{(E)-3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propenyl}phenyl)acrylate in 8 ml of methanol. The reaction mixture is placed under an atmospheric pressure of hydrogen at room temperature for 16 hours and then filtered through Celite and rinsed with dichloromethane. The solvents are evaporated off and the residue is then purified by chromatography on a column of silica eluted with a 60/40 heptane/ethyl acetate mixture. 610 mg (94%) of methyl 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-2-hydroxyphenyl)propanoate are obtained in the form of a colorless oil.

Workup

  1. filtrationfiltered through Celite
  2. washrinsed with dichloromethane
  3. customThe solvents are evaporated off
  4. customthe residue is then purified by chromatography on a column of silica
  5. washeluted with a 60/40 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-b7e16029ab064747bc44ce31c964ffed
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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