Triethylamine → 7-Fluoro-5-methyl-2-(4'-propylbicyclohexyl-4-yl)-indan-1-one

HRID 1244189Notes

Reaction equation

HRID 1244189 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](I)[C:3]=1[CH:10]([OH:28])[C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH:19]2[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20]2)[CH2:15][CH2:14]1)=[CH2:12].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]2[C:3]=1[C:10](=[O:28])[CH:11]([CH:13]1[CH2:18][CH2:17][CH:16]([CH:19]3[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20]3)[CH2:15][CH2:14]1)[CH2:12]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 21917840HCID 21917840, compound

Product 1

HCID 120204397-Fluoro-5-methyl-2-(4'-propylbicyclohexyl-4-yl)-indan-1-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

75 g (0.15 mol) of 1-(2-fluoro-6-iodo-4-methylphenyl)-2-(4′-propyl-bicyclohexyl-4-yl)-prop-2-en-1-ol, 50 ml of triethylamine, 400 mg of palladium(II) acetate (1.8 mmol) and 960 mg (3.7 mmol) of triphenylphosphine are dissolved in 200 ml of acetonitrile and refluxed overnight. The mixture is cooled down to room temperature and subjected to conventional workup.

Workup

  1. temperaturerefluxed overnight

Sources & evidence

ORD record
ord-c3eb9b4c4cff4d37ad279f5b398f2181
Source dataset
uspto-grants-2006_10
Patent number
US07122228B2

Reaction notes

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