Triethylamine → HCID 68898920, compound

HRID 493040Notes

Reaction equation

HRID 493040 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[CH:23]=[CH2:24].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(#N)C>[C:27]([O:26][C:22](=[O:25])[CH:23]=[CH:24][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:10][CH:11]=2)=[CH:16][CH:17]=1)([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 22925859HCID 22925859, compound

Product 1

HCID 68898920HCID 68898920, compoundYield 93.9%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

To 7.4 g (21.2 mmol) of 4-(tert-butoxycarbonyloxy)-4′-bromobiphenyl synthesized in the Example 9, were added 2.85 g (22.2 mmol) of tert-butyl acrylate, 10 ml of triethylamine, 30 ml of acetonitrile, 50 mg (2.22×10−1 mmol) of palladium acetate [Pd(OAc)2], and 116 mg (4.42×10−1 mmol) triphenylphosphine. The reaction system was purged with argon, and the reaction was conducted for 24 hours with heating and refluxing. The reaction mixture was poured into 500 ml of an iced water, and hydrochloric acid was added to the resultant mixture with stirring. The solid formed by stirring was collected by filtration, washed with water, dried, and recrystallized from methanol to give 7.9 g (19.9 mmol) of tert-butyl-4-(4′-tert-butoxycarbonyloxyphenyl)cinnamate.

Workup

  1. customThe reaction system was purged with argon
  2. temperaturewith heating
  3. temperaturerefluxing
  4. additionThe reaction mixture was poured into 500 ml of an iced water, and hydrochloric acid
  5. additionwas added to the resultant mixture
  6. customThe solid formed
  7. stirringby stirring
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. customdried
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ea85ba30c7494ba3bcfbccd0533043d7
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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