Triphenylphosphine → HCID 22949954, compound

HRID 1700934Notes

Reaction equation

HRID 1700934 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[O:22][CH2:23][CH2:24][S:25][CH2:26][CH2:27]O)=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:13][O:12][C:10](=[O:11])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:27][CH2:26][S:25][CH2:24][CH2:23][O:22][CH:21]([C:18]2[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=2)[C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18319029HCID 18319029, compound

Product 1

HCID 22949954HCID 22949954, compoundYield 71.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-(4-hydroxyphenyl)propionate (1.40 g, 7.77 mmol), 2-[2-[bis(4-chlorophenyl)methoxy]ethylthio]ethanol (2.80 g, 7.80 mmol) and triphenylphosphine (2.0 g, 7.8 mmol) in dry benzene (30 ml) was treated at 22° C. with diethyl azodicarboxylate (1.34 g, 7.8) added dropwise over 5 min. After 18 h at 22° C., the reaction mixture was diluted with ethyl acetate (200 ml) washed with saturated sodium bicarbonate and dried over magnesium sulfate. Evaporation of the solvent gave an oil which was triturated in a mixture of hexane and toluene (6:4) to crystallize the triphenylphosphine oxide and the hydrazine side products. The filtrate was chromatographed on silica gel (elution ethyl acetate 0-5% in toluene) to give 2.90 g (71%) of the title material as an oil.

Workup

  1. additionadded dropwise over 5 min
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave an oil which
  6. customwas triturated in a mixture of hexane and toluene (6:4)
  7. customto crystallize the triphenylphosphine oxide
  8. customThe filtrate was chromatographed on silica gel (elution ethyl acetate 0-5% in toluene)

Sources & evidence

ORD record
ord-bcd637b1843f489a8b2ebfb40af4d2fd
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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