Methyl pivaloylacetate → HCID 19783683, compound

HRID 257646

Reaction equation

HRID 257646 reaction equation
[CH2:1]1[CH2:14][N:13]2[C:4]3[C:5]([CH2:10][CH2:11][CH2:12]2)=[C:6]([OH:9])[CH:7]=[CH:8][C:3]=3[CH2:2]1.[CH3:15][C:16]([CH3:25])([CH3:24])[C:17](=O)[CH2:18][C:19](OC)=[O:20]>ClCCl>[CH3:15][C:16]([C:17]1[O:9][C:6]2[C:7](=[CH:8][C:3]3[CH2:2][CH2:1][CH2:14][N:13]4[C:4]=3[C:5]=2[CH2:10][CH2:11][CH2:12]4)[C:19](=[O:20])[CH:18]=1)([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 99597Methyl pivaloylacetate2×HCID 1704748-Hydroxyjulolidine

Product 1

HCID 19783683HCID 19783683, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Hydroxyjulolidine (1.0 g, 5.29 mmol) and methyl 4,4-dimethyl-3-oxopentanoate (1.0 g, 6.32 mmol) were heated together under nitrogen at 200° C. for 4 hours, after which time more methyl 4,4-dimethyl-3-oxopentanoate (0.5 g, 3.16 mmol) was added and heating was continued for 2 hours. After cooling to room temperature, the reaction mixture was dissolved in dichloromethane and applied to a short column of silica gel (approx. 200 g). Elution with dichloromethane removed non-polar by-products, while subsequent elution with ether afforded 11-[1,1-dimethylethyl]-9-oxo-2,3,6,7-tetrahydro-1H,5H-[1]benzopyrano[6,7,8-ij]quinolizine (1.12 g, 71% yield) as a brown oil which solidified on standing. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

Workup

  1. temperatureheating
  2. washElution with dichloromethane removed non-polar by-products
  3. washwhile subsequent elution with ether

Sources & evidence

ORD record
ord-97536e15d77f4f32a95de4487e5c4281
Source dataset
uspto-grants-1993_11
Patent number
US05262549

Linked notes

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