Triphenylphosphine → HCID 21265833, compound

HRID 566258Notes

Reaction equation

HRID 566258 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:34][N:35]1[CH:39]=[CH:38][N:37]=[C:36]1[CH2:40][CH2:41]O.[C:43]([OH:51])(=[S:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCCC1.C(OCC)(=O)C>[C:43]([S:50][CH2:41][CH2:40][C:36]1[N:35]([CH3:34])[CH:39]=[CH:38][N:37]=1)(=[O:51])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5659642-(1-Methyl-1H-iMidazol-2-yl)ethanolHCID 178526132HCID 178526132, compound

Product 1

HCID 21265833HCID 21265833, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Triphenylphosphine (10.48 g) was dissolved in tetrahydrofuran (120 ml). To the solution were added diisopropyl azodicarboxylate (8.07 g) at 0° C. The mixture was stirred for 15 minutes at the same temperature. To the mixture were added a solution of 2-(1-methyl-2-imidazolyl)ethanol (2.52 g) in tetrahydrofuran (10 ml) and thiobenzoic acid (4.7 ml) in the order mentioned. The mixture was stirred for 2.5 hours at 0° C. and then for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate, then washed with saturated solution of sodium hydrogencarbonate in water and saturated solution of sodium chloride in water in the order mentioned. The residue was dried over anhydrous sodium sulfate and concentrated under reduced pressure, which was then subjected to column chloromatography on silica gel (developing solvent: ethyl acetate-methanol: 100:0→93:7) to give the title compound (3.52 g).

Workup

  1. stirringThe mixture was stirred for 2.5 hours at 0° C.
  2. waitfor 1 hour at room temperature
  3. washwashed with saturated solution of sodium hydrogencarbonate in water and saturated solution of sodium chloride in water in the order
  4. dry with materialThe residue was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure, which

Sources & evidence

ORD record
ord-867da67d95bc4106969ff4498f5849da
Source dataset
uspto-grants-2001_01
Patent number
US06174877B1

Reaction notes

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