Dimethylformamide → HCID 20502640, compound

HRID 851145Notes

Reaction equation

HRID 851145 reaction equation
[C:1](O)(=O)/[CH:2]=[CH:3]/C(O)=O.[CH:9]1([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]=[C:15]([C:19]3[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=3)[CH2:14]2)[CH2:11][CH2:10]1.CN(C)[CH:28]=[O:29].[Li]>O>[OH:25][C:21]1[CH:20]=[C:19]([C:15]2[CH2:14][N:13]([CH2:12][C:9]3([CH2:28][OH:29])[CH:11]=[CH:10][CH:1]=[CH:2][CH2:3]3)[CH2:18][CH2:17][CH:16]=2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 3028194LithiumHCID 20502632HCID 20502632, compound

Product 1

HCID 20502640HCID 20502640, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 g of the product of Step B, 200 ml of dimethylformamide and 4.3 g of lithium thiomethylate was refluxed for 3 hours and the mixture was cooled and poured into iced water. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 95-5 chloroform-methanol mixture to obtain 5 g of 1-[{3-(3-hydroxyphenyl)-1,2,5,6-tetrahydropyridin-1-yl}-methyl]-benzenemethanol.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturethe mixture was cooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was chromatographed over silica gel
  8. washwas eluted with a 95-5 chloroform-methanol mixture

Sources & evidence

ORD record
ord-0ba3046134a04427b73e6187dc90083d
Source dataset
uspto-grants-1983_05
Patent number
US04382942

Reaction notes

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