1-Propene, 1,1-diethoxy- → cis-N-(4'-chlorobenzyl)-2,2-diethoxy-3,6-dimethyl-4-ethoxy-3,4-dihydro-2H-pyran-5-carboxamide

HRID 487754Notes

Reaction equation

HRID 487754 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH:7][C:8](=[O:17])[C:9](=[CH:13][O:14][CH2:15][CH3:16])[C:10](=[O:12])[CH3:11])=[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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:9]2[C@H:13]([O:14][CH2:15][CH3:16])[C@H:24]([CH3:25])[C:23]([O:26][CH2:27][CH3:28])([O:22][CH2:20][CH3:21])[O:12][C:10]=2[CH3:11])=[O:17])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 1408411-Propene, 1,1-diethoxy-HCID 53883739N-(4'-chlorobenzyl)-2-ethoxymethylene-3-oxobutanamide

Product 1

HCID 86746201cis-N-(4'-chlorobenzyl)-2,2-diethoxy-3,6-dimethyl-4-ethoxy-3,4-dihydro-2H-pyran-5-carboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(4'-chlorobenzyl)-2-ethoxymethylene-3-oxobutanamide (1.4 g) and tris (6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedianato)ytterbium (0.26 g) were stirred in toluene (10 ml) whilst 1,1-diethoxyprop-1-ene (4 g) was added dropwise. The mixture was stirred at room temperature for 3 days and evaporated to dryness. The residual gum was triturated with petroleum ether b.p. 60°-80° C. to give a solid which was recrystallised from a mixture of toluene and petroleum ether b.p. 60°-80° C. to give cis-N-(4'-chlorobenzyl)-2,2-diethoxy-3,6-dimethyl-4-ethoxy-3,4-dihydro-2H-pyran-5-carboxamide (0.9 g) m.p. 97°-100° C.

Workup

  1. additionwas added dropwise
  2. customevaporated to dryness
  3. customThe residual gum was triturated with petroleum ether b.p. 60°-80° C.
  4. customto give a solid which
  5. customwas recrystallised from a mixture of toluene and petroleum ether b.p. 60°-80° C.

Sources & evidence

ORD record
ord-6f0459269a0243bdb9d1cacd2f2da108
Source dataset
uspto-grants-1994_03
Patent number
US05296613

Reaction notes

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