Triethylamine → HCID 21101248, compound

HRID 1352848Notes

Reaction equation

HRID 1352848 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH:13]=[CH2:14].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C(=O)([O-])O.[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:17]([O:16][C:12](=[O:15])/[CH:13]=[CH:14]/[C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 74653(3-Bromophenyl)acetic acidHCID 80271Tri-o-tolylphosphine

Product 1

HCID 21101248HCID 21101248, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of m-bromophenylacetic acid (4.0 g, 18.6 mmol), t-butyl acrylate (4.85 g, 37.8 mmol), triethylamine (3.8 g, 37.6 mmol), tri-o-tolylphosphine (310 mg, 1.02 mmol) and palladium acetate (130 mg, 0.580 mmol) in N,N-dimethylformamide (50 ml) was stirred for 4 hours at 50° C. and then 10 hours at 90° C. The reaction mixture was diluted with an aqueous sodium hydrogencarbonate solution and washed with ethyl acetate. The aqueous layer was acidified (about pH 3) and extracted with ethyl acetate. The organic layer was washed with an aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to give the crude subject compound (5.50 g).

Workup

  1. custom10 hours
  2. customat 90° C
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customto give the crude

Sources & evidence

ORD record
ord-a644df9f3896495ea23e71965d4d1e5e
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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