Dimethyl Sulfoxide → HCID 21221225, compound

HRID 1585172Notes

Reaction equation

HRID 1585172 reaction equation
CS(C)=O.[CH2:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH:6]1[O:14][C:15]1[C:20]([O:21][CH3:22])=[CH:19][N:18]=[C:17]([CH2:23][OH:24])[CH:16]=1.C(N(CC)CC)C>O>[CH2:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:6]1[O:14][C:15]1[C:20]([O:21][CH3:22])=[CH:19][N:18]=[C:17]([CH:23]=[O:24])[CH:16]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 21221214HCID 21221214, compound

Product 1

HCID 21221225HCID 21221225, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethyl sulfoxide solution (20 ml) of 4-(2-indanyloxy)-5-methoxy-2-pyridinemethanol (5h) (2.71 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) was added sulfur trioxide-pyridine complex (4.77 g, 30 mmol), and the mixture was stirred at room temperature for 7 hours. The reaction mixture was poured into cold water to cause precipitation of crude crystals. The crude crystals were collected by filtration, dried, and purified by silica gel column chromatography, to thereby obtain the title compound (1.95 g, yield 72%).

Workup

  1. customprecipitation of crude crystals
  2. filtrationThe crude crystals were collected by filtration
  3. customdried
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-9027dfaba2834f28aecd0eede314ac2f
Source dataset
uspto-grants-1999_08
Patent number
US05935977

Reaction notes

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