Triphenylphosphine → HCID 20157919, compound

HRID 986553Notes

Reaction equation

HRID 986553 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH:14]#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])#[C:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 1177541-TridecyneHCID 15712815Methyl 3-(2-bromophenyl)propanoate

Product 1

HCID 20157919HCID 20157919, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

Palladium acetate (60 mg) was added to a deaerated solution of methyl 3-(2-bromophenyl)propanoate (11.10 g, 25 mmole), 1-tridecyne (6.75 g) and triphenylphosphine (200 mg) in anhydrous triethylamine (100 ml) and the mixture was stirred at reflux under nitrogen for 24 hrs. After cooling, the precipitated triethylamine hydrobromide was filtered off and the filtrate was evaporated to a red oil. Chromatography on silica eluting with 1:1 dichloromethane-petrol (bp 60°-80° C.) gave the title product, 1.91 g (22%) as an oil, νmax (film) 2920, 2850, 1745 cm-1, δ(CDCl3) 0.84 (3H, distorted t, terminal CH3), 1.28 (18H, m, alkylene chain), 2.39 (2H, t, J 7 Hz; C=C--CH2), 2.62 (2H, m, ArCH2), 3.04 (2H, m, CH2CO2), 3.62 (3H, s, ester CH3), 7.12 (3H, m, arom), 7.31 (1H, m, arom).

Workup

  1. temperatureat reflux under nitrogen for 24 hrs
  2. temperatureAfter cooling
  3. filtrationthe precipitated triethylamine hydrobromide was filtered off
  4. customthe filtrate was evaporated to a red oil

Sources & evidence

ORD record
ord-cc73b5fce01f42ee832f7704b00c6812
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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