Triphenylphosphine → HCID 22949960, compound

HRID 1700930Notes

Reaction equation

HRID 1700930 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.[CH2:14]([S:26][CH2:27][CH2:28]O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].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][CH2:28][CH2:27][S:26][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 73835Ethanol, 2-(dodecylthio)-HCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 22949960HCID 22949960, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-[4-hydroxyphenyl)propionate (2.46 g, 13.6 mmol), 2-(dodecylthio)ethanol (3.40 g, 13.7 mmol) and triphenylphosphine (3.60 g, 13.8 mmol) in dry benzene (50 ml) was treated at 22° C. with diethyl azodicarboxylate (2.43 g, 13.9 mmol) added dropwise over 10 min. After 3 h at 22° C., the reaction mixture was diluted with ethyl acetate, washed with water, brine and dried (magnesium sulfate). Evaporation under reduced pressure gave an oil which was triturated with hexane to precipitate the triphenylphosphine oxide and the hydrazine side products. The filtrate was chromatographed on silica gel using a gradient of ethyl acetate (0-5%) in hexane as eluent to give 4.70 g(84%) of 3-[4-[2-(dodecylthio)ethoxy]phenyl]propanoic acid methyl ester as a white solid. Recrystallization from methanol gives white leaflets: m.p. 48° C.

Workup

  1. additionadded dropwise over 10 min
  2. washwashed with water, brine
  3. dry with materialdried (magnesium sulfate)
  4. customEvaporation under reduced pressure
  5. customgave an oil which
  6. customwas triturated with hexane
  7. customto precipitate the triphenylphosphine oxide
  8. customThe filtrate was chromatographed on silica gel using a gradient of ethyl acetate (0-5%) in hexane as eluent

Sources & evidence

ORD record
ord-e4d046258b4b46298f8cb405907f75f7
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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