Triphenylphosphine → HCID 86598976, compound

HRID 1354395Notes

Reaction equation

HRID 1354395 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[SH:28].O[CH:30]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[S:28][CH:30]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 799652,5-DichlorobenzenethiolHCID 5462977Diethyl azodicarboxylateHCID 9816137tert-butyl N-(2-hydroxy-2-phenylethyl)carbamate

Product 1

HCID 86598976HCID 86598976, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of triphenylphosphine (1.97 g), 2,5-dichlorothiophenol (0.90 g) and the product from step (a) (1.48 g) in THF (30 ml) under nitrogen at 0° C. was added diethylazodicarboxylate (1.18 ml) dropwise and the mixture was stirred at 0° C. for 45 minutes, then at room temperature for 72 h. The mixture was concentrated and the residue purified by chromatography (silica, 10% ethyl acetate/isohexane as eluent) to give the sub-title compound as a clear oil (500 mg).

Workup

  1. waitat room temperature for 72 h
  2. concentrationThe mixture was concentrated
  3. customthe residue purified by chromatography (silica, 10% ethyl acetate/isohexane as eluent)

Sources & evidence

ORD record
ord-3c9accd6e1924450b2289bc1a57ce99c
Source dataset
uspto-grants-2007_05
Patent number
US07223794B2

Reaction notes

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