HCID 20333315, compound → HCID 86612032, compound

HRID 971064Notes

Reaction equation

HRID 971064 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)[O:5][C:6]=1[CH2:7][CH2:8][OH:9].[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.N1C=CC=CC=1>O>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([O:9][CH2:8][CH2:7][C:6]2[O:5][C:4]([C:10]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=3)=[N:3][C:2]=2[CH3:1])(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 20333315HCID 20333315, compoundHCID 67089493HCID 67089493, compound

Product 1

HCID 86612032HCID 86612032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of 2-[4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-oxazol-5-yl]ethanol (2.93 g, 10 mmol) in 30 ml of pyridine 4-toluenesulfonyl chloride (1.9 g, 10 mmol) was added portionwise at room temperature. Subsequently, the reaction mixture was stirred for 5 h at room temperature, and then poured into 200 ml of water and extracted (3×) with 50 ml of dichloromethane. The combined extracts were washed with 1M HCl, an aqueous solution of sodium bicarbonate, and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated, to obtain a product, 2-[4-methyl-2-(3,4,5-trimethoxyphenyl)-1,3-oxazol-5-yl]ethyl 4-toluenesulfonate having the purity of ca. 95%.

Workup

  1. extractionextracted (3×) with 50 ml of dichloromethane
  2. washThe combined extracts were washed with 1M HCl
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2f4a71dd177b46babf140c7b11585f35
Source dataset
uspto-grants-2007_12
Patent number
US07312338B2

Reaction notes

Loading…