HCID 12543456, compound → HCID 20336525, compound

HRID 1863255Notes

Reaction equation

HRID 1863255 reaction equation
[CH2:1]([C:8]1[O:9][CH:10]=[C:11]([CH2:13][CH3:14])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS([C:19]1[CH2:20][O:21][CH2:22][CH:23]=1)(=O)=O>>[CH2:1]([C:8]1[C:19]2[CH2:20][O:21][CH2:22][C:23]=2[C:10]([OH:9])=[C:11]([CH2:13][CH3:14])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 12543456HCID 12543456, compoundHCID 20336502HCID 20336502, compound

Product 1

HCID 20336525HCID 20336525, compound

Procedure

9.4 g (50 millimoles) of 2-benzyl-4-ethyloxazole and 29.6 g. (200 millimoles) of 3-methylsulfonyl-2,5-dihydrofuran are heated for 15 hours at 150°. Unconverted sulfone is distilled off in a high vacuum. The residue is digested in methylene chloride, the undissolved constituent is filtered off, and the filtrate is extracted with 150 ml of 10% strength sodium hydroxide solution. The alkaline solution is neutralized and extracted with methylene chloride. On concentrating the methylene chloride solution, 6.2 g of 4-benzyl-6-ethyl-1,3-dihydro-furo[3,4-c]pyridine-7-ol remain. Melting point, after recrystallization from nitromethane: 148° C.

Workup

  1. distillationUnconverted sulfone is distilled off in a high vacuum
  2. filtrationthe undissolved constituent is filtered off
  3. extractionthe filtrate is extracted with 150 ml of 10% strength sodium hydroxide solution
  4. extractionextracted with methylene chloride
  5. concentrationOn concentrating the methylene chloride solution, 6.2 g of 4-benzyl-6-ethyl-1,3-dihydro-furo[3,4-c]pyridine-7-ol
  6. customMelting point, after recrystallization from nitromethane
  7. custom148° C.

Sources & evidence

ORD record
ord-f0ccb47a7c0441c59dccd7efcce76d29
Source dataset
uspto-grants-1979_09
Patent number
US04168379

Reaction notes

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