Propargyl alcohol → HCID 18665558, compound

HRID 2395370Notes

Reaction equation

HRID 2395370 reaction equation
[F:1][C:2]1[C:7](I)=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[O:10][CH2:11][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:13]=1.[CH2:20]([OH:23])[C:21]#[CH:22]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:14]1([C@@H:12]2[CH2:11][O:10][C:9]([C:3]3[C:2]([F:1])=[C:7]([C:22]#[C:21][CH2:20][OH:23])[CH:6]=[CH:5][CH:4]=3)=[N:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 18665561HCID 18665561, compound

Product 1

HCID 18665558HCID 18665558, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 4,5-dihydro-2-(2-fluoro-3-iodophenyl)-4(R)-phenyloxazole (2.28 g, 6.2 mmol), propargyl alcohol (0.22 g, 12.4 mmol) and bis(triphenylphosphine)-palladium(II) chloride (220 mg, 1.1 mmol) in triethylamine (50 ml), was stirred for 1 h under a nitrogen atmosphere, Cul (420 mg, 2.2 mmol) added and the reaction mixture stirred for a further 16 hours. Insoluble material was removed by filtration and the filtrate concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:14) to afford of 3-[3-(4,5-dihydro-4(R)-phenyloxazol-2-yl)-2-fluorophenyl]-2-propyn-1-ol (1.41 g, 77%) as off-white solids.

Workup

  1. additionCul (420 mg, 2.2 mmol) added
  2. stirringthe reaction mixture stirred for a further 16 hours
  3. customInsoluble material was removed by filtration
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:14)

Sources & evidence

ORD record
ord-5cbd760531c244dcbbdea26b80e3ca19
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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