Tributylphosphine → Ethyl 3-(2-fluoro-4-{[4-(1-hydroxybutyl)benzyl]oxy}phenyl)propanoate

HRID 732201Notes

Reaction equation

HRID 732201 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].O[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([OH:28])[CH2:25][CH2:26][CH3:27])=[CH:20][CH:19]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([OH:28])[CH2:25][CH2:26][CH3:27])=[CH:20][CH:19]=2)[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23082888Ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoateHCID 231432701-[4-(Hydroxymethyl)phenyl]butan-1-ol

Product 1

HCID 23143246Ethyl 3-(2-fluoro-4-{[4-(1-hydroxybutyl)benzyl]oxy}phenyl)propanoateYield 52%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of ethyl 3-(2-fluoro-4-hydroxyphenyl)propanoate (2.12 g, 10.0 mmol), 1-[4-(hydroxymethyl)phenyl]-butane-1-ol (1.80 g, 10.0 mmol) and tributylphosphine (4.04 mL, 20.0 mmol) in toluene (150 mL) was stirred under ice-cooling and 1,1′-(azodicarbonyl)dipiperidine (5.04 g, 20.0 mmol) was added by small portions. The mixture was warmed to room temperature and stirred for 22 hr. Hexane (75 mL) was added to the reaction mixture, and precipitated insoluble material was filtered off. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-30:70) to give the title compound as a colorless oil (1.93 g, yield 52%).

Workup

  1. temperaturecooling
  2. customprecipitated insoluble material
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-30:70)

Sources & evidence

ORD record
ord-ad389274a5834804ba264ab1047fc4d8
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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