Tributylphosphine → HCID 23082820, compound

HRID 2422284Notes

Reaction equation

HRID 2422284 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.[CH3:14][C:15]1[CH:16]=[C:17]([CH:27]=[CH:28][CH:29]=1)[O:18][C:19]1[CH:20]=[C:21]([CH2:25]O)[CH:22]=[CH:23][CH:24]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[CH3:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][C:17]1[CH:16]=[C:15]([CH:29]=[CH:28][CH:27]=1)[CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 23083121[3-(3-Methylphenoxy)phenyl]methanol

Product 1

HCID 23082820HCID 23082820, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of methyl 3-(4-hydroxyphenyl)propanoate (0.396 g, 2.20 mmol), [3-(3-methylphenoxy)phenyl]methanol (0.429 g, 2.00 mmol) and tributylphosphine (0.747 mL, 3.00 mmol) in toluene (30 mL) was stirred under ice-cooling, 1,1′-(azodicarbonyl)dipiperidine (0.757 g, 3.00 mmol) was added by small portions, the temperature was raised to room temperature and the mixture was stirred for 18 hrs. Hexane (15 mL) was added to the reaction mixture, the precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane-20% ethyl acetate/hexane) and preparative HPLC (10-95% acetonitrile/water, containing 0.1% trifluoroacetic acid) to give the title compound (0.414 g, yield 55%) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane-20% ethyl acetate/hexane) and preparative HPLC (10-95% acetonitrile/water, containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-d3d33c8b22534448abd0b87696b05cac
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

Loading…