Tetrahydrofuran → HCID 15007051, compound

HRID 1613927Notes

Reaction equation

HRID 1613927 reaction equation
CN(P(N(C)C)N(C)C)C.O1[CH2:15][CH2:14][CH2:13][CH2:12]1.[CH:16]([C:18]1[C:27]([CH3:28])=[C:26]([O:29][C:30](=[O:32])[CH3:31])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1)=O>O>[CH:16](/[C:18]1[C:27]([CH3:28])=[C:26]([O:29][C:30](=[O:32])[CH3:31])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1)=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:12][CH2:13][CH2:14][CH3:15].[CH:16](/[C:18]1[C:27]([CH3:28])=[C:26]([O:29][C:30](=[O:32])[CH3:31])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 15355Hexamethylphosphorous triamideHCID 15007049HCID 15007049, compound

Product 2

HCID 15007050HCID 15007050, compoundYield 10%HCID 15007051HCID 15007051, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

This solution was cooled to -78° C., after which 1.43 g (8 mmols) of hexamethylphosphorus triamide was added and stirred for 5 minutes, followed by further addition of 2 ml of a tetrahydrofuran solution of 91.6 mg (0.40 mmols) of 2-formyl-3-methyl-4-acetoxyquinoline and stirring at -78° C. for 15 minutes and subsequently at -42° C. for 30 minutes. The reaction mixture was added to 20 ml of water and extracted with ethyl acetate, followed by washing with a saturated sodium chloride aqueous solution and drying with sodium sulfate. After removal of the solvent by distillation under reduced pressure, the residue was purified by silica gel column chromatography [Wako Gel C-200 (available from Wako Junyaku Co., Ltd.) (solvent n-hexane : ethyl acetate=15:1)] to obtain 13 mg of 2-(trans-1-nonenyl)-3-methyl-4-acetoxyquinoline (yield 10%) and 15 mg of 2-(cis-1-nonenyl)-3-methyl-4-acetoxyquinoline (yield 12%).

Workup

  1. stirringstirring at -78° C. for 15 minutes and subsequently at -42° C. for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washby washing with a saturated sodium chloride aqueous solution
  4. dry with materialdrying with sodium sulfate
  5. customAfter removal of the solvent
  6. distillationby distillation under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [Wako Gel C-200 (available from Wako Junyaku Co., Ltd.) (solvent n-hexane : ethyl acetate=15:1)]

Sources & evidence

ORD record
ord-c95a76f2966b456dac85a2d7cddc0713
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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