Ethyl Acrylate → HCID 70157968, compound

HRID 2227516Notes

Reaction equation

HRID 2227516 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45]([O:49][CH2:50][CH3:51])(=[O:48])[CH:46]=[CH2:47]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[C:13]([O:12][C:10]([CH2:9][S:8][C:5]1[CH:6]=[CH:7][C:2]([CH:47]=[CH:46][C:45]([O:49][CH2:50][CH3:51])=[O:48])=[CH:3][CH:4]=1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 54525745HCID 54525745, compound

Product 1

HCID 70157968HCID 70157968, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

3.46 g of t-butyl [(4-bromophenyl)thio]acetate was mixed with 8 ml diisopropylethylamine, 0.6 g of triphenylphosphine, 5.2 ml ethyl acrylate and 35 ml acetonitrile to form a solution. 0.26 g of palladium acetate was further added to the solution and refluxed under a stream of argon for 44 hours. The reaction mixture was extracted with ethyl acetate, washed with water. The aqueous layer was further extracted with ethyl acetate. The combined ethyl acetate layers were washed with water and brine, and then dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated and purified via column chromatography on silica gel (ethyl acetate:hexane=1:20) to give ethyl 4-[[(t-butoxycarbonyl)methyl]thio]cinnamate (2.7 g, 73.7%).

Workup

  1. customto form a solution
  2. temperaturerefluxed under a stream of argon for 44 hours
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous layer was further extracted with ethyl acetate
  6. washThe combined ethyl acetate layers were washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe drying agent was filtered off
  9. concentrationthe filtrate was concentrated
  10. custompurified via column chromatography on silica gel (ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-6b94c114f0394323af990151031958e5
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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