Tributylphosphine → HCID 23159931, compound

HRID 2110876Notes

Reaction equation

HRID 2110876 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][N:15]1[C:19]([CH3:20])=[C:18]([C:21]2[CH:22]=[C:23]([CH2:27]O)[CH:24]=[CH:25][CH:26]=2)[C:17]([CH3:29])=[N:16]1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[CH3:14][N:15]1[C:19]([CH3:20])=[C:18]([C:21]2[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=2)[CH2:27][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=2)[C:17]([CH3:29])=[N:16]1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 23159841HCID 23159841, compound

Product 1

HCID 23159931HCID 23159931, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

A solution of methyl 3-(4-hydroxyphenyl)propanoate (0.541 g, 3.00 mmol), [3-(1,3,5-trimethyl-1H-pyrazol-4-yl)phenyl]methanol (0.433 g, 2.00 mmol) and tributylphosphine (0.747 mL, 3.00 mmol) in toluene (30 mL) was stirred under ice-cooling, and 1,1′-(azodicarbonyl)dipiperidine (0.757 g, 3.00 mmol) was added by small portions. The mixture was allowed to warm to room temperature and the mixture was stirred for 22 hr. 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 column chromatography (30%-70% ethyl acetate/hexane) to give the title compound (0.406 g, yield 54%) 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 column chromatography (30%-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-20e63aad8c9e49118fd042a872748c51
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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