Triethylamine → HCID 57925878, compound

HRID 1013549Notes

Reaction equation

HRID 1013549 reaction equation
[CH3:1][P:2]([O:6]CC)[O:3][CH2:4][CH3:5].Br[C:10]1[CH:11]=[C:12](/[CH:16]=[CH:17]/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[CH:14][CH:15]=1.C(N(CC)CC)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:4]([O:3][P:2]([C:10]1[CH:11]=[C:12](/[CH:16]=[CH:17]/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[CH:14][CH:15]=1)([CH3:1])=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85063Diethyl methylphosphoniteHCID 11196821HCID 11196821, compound

Product 1

HCID 57925878HCID 57925878, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

Diethyl methylphosphonite (0.15 ml, 0.992 mmol), tert-butyl (2E)-3-(3-bromophenyl)acrylate (0.25 g, 0.883 mmol), triethylamine (0.37 ml, 2.65 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.1559 g, 0.135 mmol) were combined and allowed to heat at 100° C. for approximately eight hours. The reaction was cooled and filtered over celite, washing with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane. MS: calc'd 311 (MH+), exp 311 (MH+).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered over celite
  3. washwashing with ethyl acetate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-639281bdc1094056b3330281c0022727
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

Loading…