HCID 5323667, compound → 1,3-Dihydro-4-(phenylmethyl)furo[3,4-c]pyridin-7-ol

HRID 1863254Notes

Reaction equation

HRID 1863254 reaction equation
[CH2:1]([C:8]1[O:9][CH:10]=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS([C:17]1[CH2:18][O:19][CH2:20][CH:21]=1)(=O)=O>>[CH2:1]([C:8]1[C:17]2[CH2:18][O:19][CH2:20][C:21]=2[C:10]([OH:9])=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 5323667HCID 5323667, compoundHCID 12543456HCID 12543456, compound

Product 1

HCID 203925311,3-Dihydro-4-(phenylmethyl)furo[3,4-c]pyridin-7-ol

Procedure

11.2 g (70 millimoles) of 2-benzyloxazole and 10.5 g (70 millimoles) of 3-methylsulfonyl-2,5-dihydrofuran are heated for 7 hours at 160°. The unconverted starting compounds are distilled off in a high vacuum and the distillation residue is extracted with methylene chloride. The 4-benzyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol contained in the extract is separated off by chromatography over silica gel (using methylene chloride and ethyl acetate). 4.3 g are obtained. Recrystallization from benzene/methylene chloride gives a pure product.

Workup

  1. distillationThe unconverted starting compounds are distilled off in a high vacuum
  2. extractionthe distillation residue is extracted with methylene chloride
  3. customis separated off by chromatography over silica gel (using methylene chloride and ethyl acetate)
  4. custom4.3 g are obtained
  5. customRecrystallization from benzene/methylene chloride
  6. customgives a pure product

Sources & evidence

ORD record
ord-85780e1a6a624dc38bbd7ad7066acdf8
Source dataset
uspto-grants-1979_09
Patent number
US04168379

Reaction notes

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