Triethylamine → HCID 14888724, compound

HRID 487811Notes

Reaction equation

HRID 487811 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][CH:3]=1.[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[CH:20]=[CH2:21].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:25][C:24]([CH3:27])([O:23][C:19](=[O:22])/[CH:20]=[CH:21]/[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:4][CH:3]=1)[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 14888723HCID 14888723, compound

Product 1

HCID 14888724HCID 14888724, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of benzyl 2-(4-bromophenyl)acetate (33.5 g. 0.11 mol), t-butyl acrylate (31.6 mL, 0.22 mol) and triethylamine (85 mL. 0.64 mol) in DMF (1000 mL) was deoxygenated with argon, whereupon bis(triphenylphosphine)palladium dichloride (5.1 g. 8.3 mmol) was added. After heating at 75° C. for 12 hours the solvent was removed in vacuo providing a brown residue that was purified by chromatography on silica gel using a mixture of hexanes and ethyl acetate (9:1) to give benzyl (E)-2-[4-[3-(1,1-dimethylethoxy)-3-oxo-1-propenyl]phenyl]acetate as a pale yellow oil (23.3 g. 0.07 mol) in 60% yield.

Workup

  1. additionwas added
  2. customwas removed in vacuo
  3. customproviding a brown residue that
  4. customwas purified by chromatography on silica gel using
  5. additiona mixture of hexanes and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-d4728514b09c492aabb2e20109d39940
Source dataset
uspto-grants-1994_03
Patent number
US05296608

Reaction notes

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