Tetrabutylammonium Fluoride → HCID 22161798, compound

HRID 1088810Notes

Reaction equation

HRID 1088810 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][C:16]([CH3:23])([CH3:22])[CH:15]2[O:24][CH3:25])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>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][C:16]([CH3:22])([CH3:23])[CH:15]2[O:24][CH3:25]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22161763HCID 22161763, compound

Product 1

HCID 22161798HCID 22161798, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 8-(t-butyldimethylsilyloxymethyl)-4-methoxy-3,3-dimethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (1.40 g) in tetrahydrofuran (20 ml), 1M solution (4.2 ml) of tetrabutylammonium fluoride in tetrahydrofuran was added dropwise under ice-cooling. After the mixture was stirred for 45 minutes, tetrahydrofuran was distilled off and the residue was extracted with dichloromethane. The extract was 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-hydroxymethyl-4-methoxy-3,3-dimethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (0.75 g).

Workup

  1. temperaturecooling
  2. distillationtetrahydrofuran was distilled off
  3. extractionthe residue was extracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (6:1)]

Sources & evidence

ORD record
ord-4f9fbc600551443ab4c6fcb0cf982d23
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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