Benzyl Alcohol → {5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(phenylmethyl)oxy]-2-pyridinyl}methyl acetate

HRID 15157Notes

Reaction equation

HRID 15157 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O.[C:34]([O:37][CH2:38][C:39]1[NH:40][CH:41]=[C:42]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][C:51]([O:54][CH3:55])=[CH:50][CH:49]=2)[C:43](=[O:45])[CH:44]=1)(=[O:36])[CH3:35].[CH2:56](O)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>O1CCCC1>[C:34]([O:37][CH2:38][C:39]1[CH:44]=[C:43]([O:45][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:42]([O:46][CH2:47][C:48]2[CH:49]=[CH:50][C:51]([O:54][CH3:55])=[CH:52][CH:53]=2)=[CH:41][N:40]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 66598536[5-[(4-methoxyphenyl)methoxy]-4-oxo-1H-pyridin-2-yl]methyl acetate

Product 1

HCID 67526761{5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(phenylmethyl)oxy]-2-pyridinyl}methyl acetateYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of triphenylphosphine (39.3 g, 150 mmol) in tetrahydrofuran (600 ml) was treated at 0° C. with bis(1-methylethyl) (E)-1,2-diazenedicarboxylate (30 ml, 152 mmol). After 10 minutes [5-({[4-(methoxy)phenyl]methyl}oxy)-4-oxo-1,4-dihydro-2-pyridinyl]methyl acetate (33.5 g, 110 mmol) (for a synthesis, see WO2004058144, Example 60(c)) was added. After 10 minutes benzyl alcohol (12.4 ml, 120 mmol) was added and the mixture was stirred overnight. Evaporation and chromatography on silica eluting with 20-50% ethyl acetate in hexane afforded an oil (26.3 g, 61%).

Workup

  1. additionwas added
  2. customEvaporation and chromatography on silica eluting with 20-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-99928ac1caa449338e9a2b2199c455a7
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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