2,5-Dihydrofuran → HCID 20392495, compound

HRID 1863256Notes

Reaction equation

HRID 1863256 reaction equation
[CH2:1]([C:8]1O[C:10]([O:16]CC)=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:19]1[CH2:23][CH:22]=[CH:21][CH2:20]1>>[CH2:1]([C:8]1[C:21]2[CH2:20][O:19][CH2:23][C:22]=2[C:10]([OH:16])=[C:11]([CH:13]([CH3:14])[CH3:15])[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 155702,5-DihydrofuranHCID 20392533HCID 20392533, compound

Product 1

HCID 20392495HCID 20392495, compound

Procedure

36.8 g of 2-benzyl-4-isopropyl-5-ethoxyoxazole (150 millimoles) and 210 g (3 moles) of 2,5-dihydrofuran are heated in an autoclave at 190° C. for 5 hours. Unconverted 2,5-dihydrofuran is distilled off. The residue is taken up in methylene chloride and the solution is extracted with 10% strength sodium hydroxide solution. On neutralizing the alkaline solution, crude 4-benzyl-6-isopropyl-1,3-dihydro-furo[3,4-c]pyridin-7-ol is obtained and is extracted with methylene chloride (20.4 g). The product is converted to the hydrochloride by means of dilute hydrochloric acid and the hydrochloride is recrystallized from ethanol; melting point 232°-233° C.

Workup

  1. distillationUnconverted 2,5-dihydrofuran is distilled off
  2. extractionthe solution is extracted with 10% strength sodium hydroxide solution

Sources & evidence

ORD record
ord-e731d661763e431ab68ec403e1912c3d
Source dataset
uspto-grants-1979_09
Patent number
US04168379

Reaction notes

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