Water → 2-(2-Decylindan-5-yl)-5-(3-phenylpropyloxy)pyrimidine

HRID 2211073Notes

Reaction equation

HRID 2211073 reaction equation
[CH2:1]([CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]3[N:25]=[CH:24][C:23]([OH:26])=[CH:22][N:21]=3)[CH:17]=2)[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C1(C)C=CC(S(O[CH2:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)(=O)=O)=CC=1.[OH-].[K+].O>C(O)C>[CH2:1]([CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:20]3[N:25]=[CH:24][C:23]([O:26][CH2:37][CH2:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:22][N:21]=3)[CH:17]=2)[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 109899213-Phenylpropyl 4-methylbenzenesulfonateHCID 193753532-(2-Decylindan-5-yl)pyrimidine-5-ol

Product 1

HCID 193753602-(2-Decylindan-5-yl)-5-(3-phenylpropyloxy)pyrimidineYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.443 g of 2-(2-decylindan-5-yl)pyrimidine-5-ol, 0.343 g of phenylpropyl p-toluenesulfonate and 0.1 g of potassium hydroxide were dissolved in 2 ml of ethanol, followed by heat-refluxing for 4 hours. After the reaction, the reaction mixture was poured into water and subjected to extraction with toluene. The resultant organic layer was washed with water and dried with anhydrous sodium sulfate, followed by distilling-off of the solvent and purification by silica gel column chromatography to obtain 0.313 g of an objective product (Yield: 53.2%).

Workup

  1. temperatureby heat-refluxing for 4 hours
  2. customAfter the reaction
  3. extractionsubjected to extraction with toluene
  4. washThe resultant organic layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationfollowed by distilling-off of the solvent and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-7a8d88ac4e4845b1bd644afc12d679ed
Source dataset
uspto-grants-1995_10
Patent number
US05462694

Reaction notes

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