Sodium hydride → 2,3-Dimethyl-6-t-butyl-8-fluoro-4-methoxyacetylquinoline

HRID 1005949Notes

Reaction equation

HRID 1005949 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:13]([CH3:14])=[C:12](O)[C:11]2[C:6](=[C:7]([F:20])[CH:8]=[C:9]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]=2)[N:5]=1.[CH3:21][O:22][CH2:23][C:24](Cl)=[O:25]>O1CCCC1>[CH3:3][C:4]1[C:13]([CH3:14])=[C:12]([C:24](=[O:25])[CH2:23][O:22][CH3:21])[C:11]2[C:6](=[C:7]([F:20])[CH:8]=[C:9]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 96623Methoxyacetyl chlorideHCID 178432297HCID 178432297, compound

Product 1

HCID 699185872,3-Dimethyl-6-t-butyl-8-fluoro-4-methoxyacetylquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In tetrahydrofuran (10 ml) was suspended 60% sodium hydride (165 mg). The compound 1 (680 mg) was added to the suspension under ice cooling, and the mixture was stirred for 30 min. Further, methoxyacetyl chloride (200 μl) was added thereto, and the mixture was stirred for 3 hr. The reaction solution thus obtained was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine and was then dried over anhydrous sodium sulfate. The solvent was then removed under the reduced pressure. The crude product was purified by chromatography on silica gel (Wako Gel C-200, elution solvent: n-hexane-ethyl acetate (3:1)) to give 2,3-dimethyl-6-t-butyl-8-fluoro-4-methoxyacetylquinoline (compound 10, 390 mg). 1H-NMR data on this compound in deutro-chloroform were as shown below.

Workup

  1. stirringthe mixture was stirred for 3 hr
  2. customThe reaction solution thus obtained
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. customThe solvent was then removed under the reduced pressure
  7. customThe crude product was purified by chromatography on silica gel (Wako Gel C-200, elution solvent: n-hexane-ethyl acetate (3:1))

Sources & evidence

ORD record
ord-32483b105b234e888831fcebe5591c94
Source dataset
uspto-grants-2004_09
Patent number
US06787557B2

Reaction notes

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