Water → HCID 14685736, compound

HRID 1088798Notes

Reaction equation

HRID 1088798 reaction equation
[Si]([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][CH2:23][CH:24]=[CH2:25])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>O1CCCC1>[OH: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][CH2:23][CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 22161778HCID 22161778, compound

Product 1

HCID 14685736HCID 14685736, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-t-Butyldimethylsilyloxymethyl-4-allyloxy-1-ethyl-1,2,3,4-tetrahydroquinoline (1.81 g) was dissolved in tetrahydrofuran (20 ml), and to this solution was added dropwise 1M tetrabutylammonium fluoride-tetrahydrofuran solution (6 ml) under ice-cooling. The mixture was stirred for 1 hour at the same temperature. Water was added to the reaction mixture and after distilling off tetrahydrofuran, the residue was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and distilled off then 8-hydroxymethyl-4-allyloxy-1-ethyl-1,2,3,4-tetrahydroquinoline (1.30 g) was obtained.

Workup

  1. temperaturecooling
  2. distillationafter distilling off tetrahydrofuran
  3. extractionthe residue was extracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationdistilled off

Sources & evidence

ORD record
ord-20f6e5b17fe544c3bf58ca1e80212882
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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