1-Propene, 1,1-diethoxy- → Trans-2,2-diethoxy-3,6-dimethyl-4-acetylamino-5-(4'-chlorophenylcarbamoyl)-3,4-dihydro-2H-pyran

HRID 466280Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C:10](=[CH:14][NH:15][C:16](=[O:18])[CH3:17])[C:11](=[O:13])[CH3:12])=[CH:4][CH:3]=1.[CH2:20]([O:22][C:23]([O:26][CH2:27][CH3:28])=[CH:24][CH3:25])[CH3:21]>C1(C)C=CC=CC=1>[CH2:20]([O:22][C:23]1([O:26][CH2:27][CH3:28])[C@@H:24]([CH3:25])[C@H:14]([NH:15][C:16](=[O:18])[CH3:17])[C:10]([C:9](=[O:19])[NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[C:11]([CH3:12])[O:13]1)[CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

N-(4'-chlorophenyl)-2-(acetylaminomethylene)-3-oxobutanamide (83 g) in toluene (200 ml) was treated with 1,1-diethoxyprop-1-ene (60 ml) and heated at 100° C. for 6 hours. The mixture was evaporated and the residue was triturated with toluene to give trans-2,2-diethoxy-3,6-dimethyl-4-(acetylamino)-5-(4'-chlorophenylcarbamoyl)-3,4-dihydro-2H-pyran (80.5 g) m.p. 199°-201° C.

Workup

customThe mixture was evaporated
customthe residue was triturated with toluene

Sources & evidence

ORD record: ord-4590463a90754ed795711203045b794f
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05155236

Reaction notes

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