Tri-o-tolylphosphine → HCID 67580760, compound

HRID 1596710Notes

Reaction equation

HRID 1596710 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])=[C:6]([CH2:8][CH2:9][OH:10])[CH:7]=1.[CH2:21]([N:23]([CH2:29][CH3:30])[C:24](=[O:28])/[CH:25]=[CH:26]/[CH3:27])[CH3:22].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:21]([N:23]([CH2:29][CH3:30])[C:24](=[O:28])/[CH:25]=[C:26](/[C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[F:20])=[C:6]([CH2:8][CH2:9][OH:10])[CH:7]=1)\[CH3:27])[CH3:22]

Participants

7

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 53544532-ButenaMide, N,N-diethyl-, (E)-HCID 21702602HCID 21702602, compound

Product 1

HCID 67580760HCID 67580760, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-[5-bromo-2-[2,6-difluorobenzyloxy)phenyl]-1-ethanol (14.07 g, 41.02 mmol) and N,N-diethylcrotonamide (8.68 g, 61.53 mmol) in 60 mL triethylamine in a thick-walled pyrex tube is degassed wish nitrogen for 15 minutes. Pd(OAc)2 (0.46 g, 2.05 mmol) and tri-o-tolylphosphine (1.25 g, 4.10 mmol) are placed into the tube, which is then sealed, and the mixture is heated to 100° for 5 hours. The mixture is diluted with EtOAc (400 mL), and white precipitate is filtered out. The filtrate is then washed with 1 N HCl (2×400 mL), H20 (1×100 mL) and brine (1×100 ni), dried over MgSO4, and concentrated in vacuo. Chromatography (silica, 3:1 EtOAc/hexane) gives (E)-3-[4-(2,6-difluorobenzyloxy)-3-(2-hydroxyethyl)-phenyl]-2-butenoic acid diethy amide.

Workup

  1. customfor 15 minutes
  2. customis then sealed
  3. temperaturethe mixture is heated to 100° for 5 hours
  4. filtrationis filtered out
  5. washThe filtrate is then washed with 1 N HCl (2×400 mL), H20 (1×100 mL) and brine (1×100 ni)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1f1db60bfaa434794c8e7f4afa8bfaa
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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