Triphenylphosphine → HCID 10609721, compound

HRID 1955162Notes

Reaction equation

HRID 1955162 reaction equation
CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:34][C:35]1[CH:42]=[C:41]([OH:43])[CH:40]=[CH:39][C:36]=1[C:37]#[N:38].[S:44]1[C:48]([CH2:49]O)=[CH:47][N:46]=[CH:45]1>O1CCCC1>[F:34][C:35]1[CH:42]=[C:41]([O:43][CH2:49][C:48]2[S:44][CH:45]=[N:46][CH:47]=2)[CH:40]=[CH:39][C:36]=1[C:37]#[N:38]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 27632165-ThiazolylmethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 10609721HCID 10609721, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Diisopropylazodicarboxylate (4.0 g) was dissolved in a little anhydrous tetrahydrofuran (about 10 ml) and added dropwise to a stirred solution of triphenylphosphine (5.2 g) in anhydrous tetrahydrofuran (150 ml) at 0° C. under nitrogen. After stirring at 0 C. for 15 minutes, during which time a white precipitate formed, a mixture of 2-fluoro-4-hydroxybenzonitrile (S. M. Kelly, Helv.Chim.Acta. 1984, Volume 67, P.1572-1579) (2.0 g) and thiazole-5-methanol (2.3 g) in anhydrous tetrahydrofuran (20 ml) was added dropwise whilst maintaining the temperature at or below 5° C. The reaction mixture was stirred in the cooling bath for a further 2 hours then allowed to warm slowly to room temperature. After standing at room temperature overnight the reaction mixture was partitioned between ethyl acetate (200 ml) and saturated aqueous ammonium chloride solution (200 ml). The layers were separated and the organic phase washed with water (100 ml), dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (1:1, v/v). Fractions homogenous in the required product were combined and evaporated affording the title compound as a pale yellow solid (2.0 g).

Workup

  1. customduring which time a white precipitate formed
  2. temperaturewhilst maintaining the temperature at or below 5° C
  3. stirringThe reaction mixture was stirred in the cooling bath for a further 2 hours
  4. waitAfter standing at room temperature overnight
  5. customthe reaction mixture was partitioned between ethyl acetate (200 ml) and saturated aqueous ammonium chloride solution (200 ml)
  6. customThe layers were separated
  7. washthe organic phase washed with water (100 ml)
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe residue was purified by flash chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (1:1
  11. customevaporated

Sources & evidence

ORD record
ord-373acb2e2a154cfd89cef2bf010519ea
Source dataset
uspto-grants-2000_09
Patent number
US06124343

Reaction notes

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