Triphenylphosphine → HCID 69652275, compound

HRID 1831760Notes

Reaction equation

HRID 1831760 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:43][C:44]1[CH:49]=[C:48]([Cl:50])[CH:47]=[CH:46][C:45]=1[CH2:51][CH2:52]O>O1CCCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:52][CH2:51][C:45]2[CH:46]=[CH:47][C:48]([Cl:50])=[CH:49][C:44]=2[Cl:43])[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 88068Methyl 3-HydroxybenzoateHCID 27340992,4-Dichlorophenethyl alcoholHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 69652275HCID 69652275, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

2 g (13.1 mmol) of 3-hydroxybenzoic acid methyl ester and 4.75 g (18.1 mmol) of triphenylphosphine were dissolved in 48 ml of anhydrous tetrahydrofuran. The solution was cooled to 0° C. and a solution of 3.04 g (17.5 mmol) DEAD in 7 ml of anhydrous tetrahydrofuran was added dropwise over 20 min. The solution was stirred at RT for 45 min. and a solution of 2.76 g (14.5 mmol) of 2-(2,4-Dichlorophenyl)-ethanol in 3 ml anhydrous tetrahydrofuran was added. The reaction was stirred for 16 h at RT. The solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (4/1).

Workup

  1. stirringThe reaction was stirred for 16 h at RT
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (4/1)

Sources & evidence

ORD record
ord-e743998b5b524481b4bfff9be9b6fe7b
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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