Furfural → Oxazole, 4,5-dihydro-4,4-dimethyl-2-(2-(2-furanyl)ethenyl)-

Reaction equation

[CH:1](=O)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[O:10][CH2:11][C:12]([CH3:15])([CH3:14])[N:13]=1>>[CH3:14][C:12]1([CH3:15])[N:13]=[C:9](/[CH:8]=[CH:1]/[C:2]2[O:6][CH:5]=[CH:4][CH:3]=2)[O:10][CH2:11]1

Participants

Reactant 2

HCID 7362Furfural

HCID 744964,5-Dihydro-2,4,4-trimethyloxazole

Product 1

HCID 6445995Oxazole, 4,5-dihydro-4,4-dimethyl-2-(2-(2-furanyl)ethenyl)-

Procedure

4,4-Dimethyl-2(2-α-furylethenyl)-2-oxazoline (P-1906) was prepared by reacting furfural with 2,4,4-trimethyl-2-oxazoline. The product had a boiling point of 87° at 0.14 mm and the nmr spectrum and infra-red absorption spectrum were consistent with the proposed structure. The oral LD0 by adminstration to mice was 50 mg/kg; the LD50 was 212 and the LD100 was 300 mg/kg.

Sources & evidence

ORD record: ord-de937d0f163d4f4b9a7ff5ca53bb6eb6
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03953432

Reaction notes

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