Triphenylphosphine → 2-Hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl ester

HRID 987243Notes

Reaction equation

HRID 987243 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:21][S:22]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33]O)=[CH:28][CH:27]=1)(=[O:24])=[O:23].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3](=[O:20])[CH:4]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:33][CH2:32][C:29]2[CH:28]=[CH:27][C:26]([O:25][S:22]([CH3:21])(=[O:23])=[O:24])=[CH:31][CH:30]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 229887694-(2-Hydroxyethyl)phenyl methanesulfonateHCID 572290252-Hexyloxy-3-(4-hydroxyphenyl)propanoic acid methyl ester

Product 1

HCID 569752562-Hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Hexyloxy-3-(4-hydroxyphenyl)propanoic acid methyl ester (0.33 g, 1.19 mmole) and 2-(4-methanesulfonyloxyphenyl)ethanol (0.2578 g; 1.19 mmole) was dissolved in dichloromethane (5 ml) under argon. Azodicarbonyl dipiperidine (0.451 g; 1.789 mmole) was added followed by addition of triphenylphosphine (0.375 g; 1.423 mmole). The reaction mixture was stirred at room temperature and after 2 hours more dichloromethane (2 ml) was added. The reaction mixture was stirred for another 18 hours and then filtered. The filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine, dried with sodium sulfate and evaporated. Chromatography of the residue on silica gel using heptane:ethyl acetat (2:1 to 1:1) as eluant gave 0.381 g (67% yield) of 2-hexyloxy-3-[4-(2-{4-methanesulfonyloxyphenyl}-ethoxy)phenyl]propanoic acid methyl ester.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. washThe filtrate was washed with water, sodium hydrogen carbonate solution, diluted potassium hydrogen sulfate solution and brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-596c8c7f5368429bb572668e2b0555f0
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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