Triphenylphosphine → HCID 18944187, compound

HRID 400230Notes

Reaction equation

HRID 400230 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([OH:24])[CH2:21][C:22]#[CH:23].Br[C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=[O:29]>C(N(CC)CC)C.CCOCC.[Pd](Cl)Cl>[OH:24][CH2:20][CH2:21][C:22]#[C:23][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=[O:29]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 135663-Butyn-1-OLHCID 811292-Bromobenzaldehyde

Product 1

HCID 18944187HCID 18944187, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of palladium chloride (11.0 mg, 0.618 mmol) and cuprous iodide (Aldrich gold label, 43.5 mg, 0.229 mmol) in triethylamine (distilled from calcium hydride, 53 mL) was added, sequentially, triphenylphosphine (439 mg, 1.67 mmol), 3-butyn-1-ol (8.0 mL, 106 mmol), and 2-bromobenzaldehyde (10.6 mL, 88.3 mmol). The mixture was refluxed for 7 hours. The mixture was cooled to room temperature, diluted with ether (300 mL) and filtered. The pad was washed with ether (3×50 mL) and the combined filtrates were concentrated in vacuo to an oil: 16.1 g; 1H NMR (270 MHz, deuteriochloroform) δ 10.4 (1H, s), 7.85 (d, J=7 Hz), 7.35-7.50 (m, 3H), 3.0-4.0 (br s, 1H), 3.85 (t, J=6 Hz, 2H), 2.74 (t, J=6 Hz, 2H);

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed for 7 hours
  3. filtrationfiltered
  4. washThe pad was washed with ether (3×50 mL)
  5. concentrationthe combined filtrates were concentrated in vacuo to an oil

Sources & evidence

ORD record
ord-a247eb3b6c274b088b9e94d99e92b082
Source dataset
uspto-grants-1998_10
Patent number
US05827868

Reaction notes

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