HCID 12708700, compound → HCID 20392478, compound

HRID 1863246Notes

Reaction equation

HRID 1863246 reaction equation
CS([C:5](=[CH:9][CH2:10][O:11][CH3:12])[CH2:6][O:7][CH3:8])(=O)=O.[CH2:13]([C:20]1[O:21][CH:22]=[C:23]([CH3:25])[N:24]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:25][C:23]1[C:22]([OH:21])=[C:5]([CH2:6][O:7][CH3:8])[C:9]([CH2:10][O:11][CH3:12])=[C:20]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:24]=1

Participants

3

Reactant 2

HCID 12708700HCID 12708700, compoundHCID 54174822HCID 54174822, compound

Product 1

HCID 20392478HCID 20392478, compound

Conditions

Temperature
190 °C

Procedure

A mixture of 19.4 g (0.1 mole) of 2-methylsulfonyl-1,4-dimethoxy-but-2-ene and 34.6 g (0.2 mole) of 2-benzyl-4-methyloxazole is heated for 10 hours at 190° C. After it has cooled, unconverted oxazole and sulfone are distilled off in a high vacuum. The residue is chromatographed over silica gel (using ethyl acetate and methanol). 5.5 g of 2-methyl-4,5-di-(methoxymethyl)-6-benzyl-pyridin-3-ol, identified by the NMR spectrum, are obtained.

Workup

  1. temperatureAfter it has cooled
  2. distillationunconverted oxazole and sulfone are distilled off in a high vacuum
  3. customThe residue is chromatographed over silica gel (using ethyl acetate and methanol)
  4. customare obtained

Sources & evidence

ORD record
ord-4f98345f1135495b9e1db28f5cff29fe
Source dataset
uspto-grants-1979_09
Patent number
US04168379

Reaction notes

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