Water → HCID 86642715, compound

HRID 1361094Notes

Reaction equation

HRID 1361094 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](I)[CH:12]=[CH:11][C:10]=1/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:29]([S:33]([O:36][C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH:44]=[CH2:45])=[CH:39][C:38]=1[O:46][CH3:47])(=[O:35])=[O:34])[CH2:30][CH2:31][CH3:32].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13](/[CH:45]=[CH:44]/[CH2:43][C:40]2[CH:41]=[CH:42][C:37]([O:36][S:33]([CH2:29][CH2:30][CH2:31][CH3:32])(=[O:34])=[O:35])=[C:38]([O:46][CH3:47])[CH:39]=2)[CH:12]=[CH:11][C:10]=1/[CH:16]=[CH:17]/[C:18]([O:20][CH3:21])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 66971914HCID 66971914, compoundHCID 86642396HCID 86642396, compound

Product 1

HCID 86642715HCID 86642715, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 27342162-(Dicyclohexylphosphino)biphenylCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

71 mg (0.2 mmol) of 2-(dicyclohexylphosphino)biphenyl and 23 mg (0.1 mmol) of palladium acetate are added to a solution of 2 g (5.07 mmol) of methyl(E)-3-(2-benzyloxy-4-iodophenyl)acrylate, 1.1 ml (7.6 mmol) of triethylamine and 2.9 g (5.07 mmol) of 4-allyl-2-methoxyphenyl 1-butane-1-sulfonate in 20 ml of dimethylformamide. The reaction mixture is heated at 80° C. for 4 hours. The reaction is treated by addition of 50 ml of water and then extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over sodium sulfate and filtered, and the solvents are then evaporated off. The residue is purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 2.53 g (91%) of methyl(E)-3-(2-benzyloxy-4-{(E)-3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propenyl}phenyl)acrylate are obtained in the form of a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvents are then evaporated off
  6. customThe residue is purified by chromatography on a column of silica
  7. washeluted with a 90/10 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-3119ce6169c9447b80471842c73a8d33
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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