Pyridine → HCID 53806132, compound

HRID 261145Notes

Reaction equation

HRID 261145 reaction equation
[C:1]([CH:3]([OH:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)#[N:2].N1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CC[O:26][CH2:27][CH3:28]>C1C=CC=CC=1>[CH:8]([CH:28]([C:19]1[CH:6]=[CH:5][C:4]2[C:21](=[CH:22][CH:23]=[CH:1][CH:3]=2)[CH:20]=1)[C:27]([O:17][CH:3]([C:1]#[N:2])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)=[O:26])([CH3:9])[CH3:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3283Diethyl EtherHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-

Product 1

HCID 53806132HCID 53806132, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of α-isopropyl-2-naphthlyacetyl chloride (219 g, 0.887 mole) in benzene (350 ml) is added to a solution of α-cyano-m-phenoxybenzyl alcohol (179.8 g, 0.798 mole) and pyridine (70.2 g, 0.887 mole) in ether (750 ml) at 0°-10° C. over a 11/2 hour period. Pyridine hydrochloride precipitates out during the addition. The reaction mixture, after stirring overnight at room temperature, is diluted with more ether (500 ml) and poured into water (1200 ml). The organic phase is separated, washed with water, 10% H2SO4 and water and dried over Na2SO4. Evaporation gives an orange-brown gum (348 g, 100% crude yield, 87.5% pure by liquid chromatography).

Workup

  1. customPyridine hydrochloride precipitates out during the addition
  2. additionis diluted with more ether (500 ml)
  3. additionpoured into water (1200 ml)
  4. customThe organic phase is separated
  5. washwashed with water, 10% H2SO4 and water
  6. dry with materialdried over Na2SO4
  7. customEvaporation
  8. customgives an orange-brown gum (348 g, 100% crude yield, 87.5% pure by liquid chromatography)

Sources & evidence

ORD record
ord-1196557bca1e4527865dd7c262393feb
Source dataset
uspto-grants-1979_08
Patent number
US04164415

Reaction notes

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