Water → HCID 22161778, compound

HRID 1088797Notes

Reaction equation

HRID 1088797 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]([CH2:20][CH3:21])[CH2:17][CH2:16][CH:15]2[OH:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27].O>CN(C)C=O>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]([CH2:20][CH3:21])[CH2:17][CH2:16][CH:15]2[O:22][CH2:27][CH:26]=[CH2:25])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromide2×HCID 24758Sodium hydride2×HCID 22161771HCID 22161771, compound

Product 1

HCID 22161778HCID 22161778, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-t-butyldimethylsilyloxymethyl-4-hydroxy-1-ethyl-1,2,3,4-tetrahydroquinoline (2.19 g) was dissolved in dimethyl formamide (15 ml), followed by addition of sodium hydride (60% in oil, 0.33 g), and allyl bromide (0.99 g) was added thereto under ice-cooling. The mixture was stirred for 2.5 hours at the same temperature. Furthermore sodium hydride (60% in oil, 0.16 g) and allyl bromide (0.48 g) were added to the reaction mixture and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture. The mixture was extracted with ethyl acetate-toluene and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (6 : 1)]to give 8-t-butyldimethylsilyloxymethyl-4-allyloxy-1-ethyl-1,2,3,4-tetrahydroquinoline (1.83 g).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringthe mixture was stirred overnight at room temperature
  4. extractionThe mixture was extracted with ethyl acetate-toluene
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resulting residue was purified by silica gel column chromatography [eluent

Sources & evidence

ORD record
ord-a2cb982b580145e99b117cdbe9de55d1
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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