Pyridine → HCID 14817171, compound

HRID 274181Notes

Reaction equation

HRID 274181 reaction equation
N1C=CC=CC=1.[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:16][N:15]=2)=[CH:10][CH:9]=1.[C:31]([O:38][CH:39]([C:41]1[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[CH:43][CH:42]=1)[CH3:40])(=[O:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>O>[C:31]([O:38][CH:39]([C:41]1[CH:49]=[CH:48][C:44]([C:45]([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[N:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:16][N:15]=3)=[CH:12][CH:13]=2)=[O:46])=[CH:43][CH:42]=1)[CH3:40])(=[O:37])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 1049PyridineHCID 14675888HCID 14675888, compoundHCID 135585896110203-06-0

Product 1

HCID 14817171HCID 14817171, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 20 ml of pyridine were dissolved 1.97 g (6 millimoles) of 2-(4-hydroxyphenyl)-5-decyloxypyrimidine, and then 1.41 g (5 millimoles) of an acid chloride derived from (+)-4-(1-hexanoyloxyethyl)benzoic acid were added thereto, to subject to reaction at 30° to 40° C. for 2 hours. After completion of the reaction, the reaction mixture was poured into 200 ml of water, adjusted to pH 3 to 4 with hydrochlolic acid, followed by extraction with 200 ml of toluene, and the organic phase was washed with water, 5% aqueous sodium hydrogen carbonate solution and water in this order and then the organic phase was dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate) to obtain 2.76 g (yield: 96%) of 4-(5-decyloxy-2-pyrimidyl)phenyl (+)-4-(1-hexanoyloxyethyl)benzoate.

Workup

  1. additionwere added
  2. customto subject to reaction at 30° to 40° C. for 2 hours
  3. customAfter completion of the reaction
  4. extractionfollowed by extraction with 200 ml of toluene
  5. washthe organic phase was washed with water, 5% aqueous sodium hydrogen carbonate solution and water in this order
  6. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate)

Sources & evidence

ORD record
ord-c3b12f70cd074080a06bc836f032d1db
Source dataset
uspto-grants-1995_02
Patent number
US05389293

Reaction notes

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