Triphenylphosphine → HCID 23371885, compound

HRID 1900049Notes

Reaction equation

HRID 1900049 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)[CH2:5]1.C1(P([C:30]2[CH:35]=[CH:34]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[Li+].C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.C([Sn](CCCC)(CCCC)C1CC1)CCC.[OH-].[Na+]>CN(C=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH:34]1([C:13]2[CH:14]=[CH:15][C:10]([N:6]3[CH2:5][CH:4]([CH2:3][O:2][CH3:1])[O:8][C:7]3=[O:9])=[CH:11][CH:12]=2)[CH2:35][CH2:30]1

Participants

10

Reactant 6

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 433294Lithium ChlorideHCID 10947505CyclopropyltributylstannaneHCID 23371883HCID 23371883, compound

Product 1

HCID 23371885HCID 23371885, compoundYield 19.3%

Reagents, catalysts & solvents 3

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.0 g (10.48 mmol) of (RS)-5-methoxymethyl-3-(4-bromo-phenyl)-oxazolidin-2-one, 6.29 g (6.29 mmol) of triphenylphosphine, 0.88 g (1.25 mmol) of bis(triphenylphosphine)palladium-II dichloride, 3.73 g of lithium chloride, 1 spatula tip of 2,6-di-tert-butyl-p-cresol and 6.94 g of tributyl-cyclopropylstannane in 50 ml of DMF were stirred at 120° for 6 hours. The reaction mixture was treated with water and 1N sodium hydroxide solution and extracted with ether. The crude product obtained was chromatographed on a 30-fold amount of silica gel. The extracts which were uniform according to tlc (silica gel, ethyl acetate-hexane 1:1) were pooled and the solvent was distilled off. 0.3 g of colorless crystals was obtained from tert-butyl methyl ether/hexane. M.p. 58°-60°.

Workup

  1. extractionextracted with ether
  2. customThe crude product obtained
  3. customwas chromatographed on a 30-fold amount of silica gel
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-199efd6287b942199735b5ed4e5280ec
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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