HCID 86761272, compound → HCID 86761271, compound

HRID 1361084Notes

Reaction equation

HRID 1361084 reaction equation
C([O:8][C:9]1[CH:10]=[C:11](/[CH:34]=[CH:35]/[C:36]([O:38][CH3:39])=[O:37])[CH:12]=[CH:13][C:14]=1/[CH:15]=[CH:16]/[CH2:17][C:18]1[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]=1)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:14]2[CH:13]=[CH:12][C:11]([CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])=[CH:10][C:9]=2[OH:8])=[CH:19][C:20]=1[O:32][CH3:33])(=[O:27])=[O:26])[CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 2

HCID 86761272HCID 86761272, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86761271HCID 86761271, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

11 g (20 mmol) of methyl(E)-3-(3-benzyloxy-4-{(E)-3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propenyl}phenyl)acrylate are dissolved in 100 ml of methanol and 1.1 g (10% massique) palladium-on-charcoal are then added. The reaction medium est placed under 1 atmosphere of hydrogen for 24 hours, and then filtered through Celite and rinsed with dichloromethane, and the filtration liquors are concentrated. The residue is purified by chromatography on a column of silica eluted with an 8/2 heptane/ethyl acetate mixture. 8 g (73%) of methyl 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-3-hydroxyphenyl)propanoate are obtained.

Workup

  1. filtrationfiltered through Celite
  2. washrinsed with dichloromethane
  3. filtrationthe filtration liquors
  4. concentrationare concentrated
  5. customThe residue is purified by chromatography on a column of silica
  6. washeluted with an 8/2 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-c47531890346446d96cb8d749160f196
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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