Tetrabutylammonium Fluoride → HCID 66996598, compound

HRID 521263Notes

Reaction equation

HRID 521263 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:15]=[CH:14]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[N:13]1([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[CH:17][C:16]=2[N:15]=[CH:14]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22320486HCID 22320486, compound

Product 1

HCID 66996598HCID 66996598, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 1-[4-(tert-butyldimethylsilanyloxy)butyl]-1H-imidazo[4,5-c]quinoline (46.0 g, 129 mmol) from the previous step and tetrabutylammonium fluoride (142 mL of a 1 M solution in THF) were dissolved in THF (400 mL) and stirred for 1 hour, then concentrated under reduced pressure to provide 4-(1H-imidazo[4,5-c]quinolin-1-yl)butan-1-ol (20.0 g) as a light brown solid after chromatography on silica gel (elution with 10% methanol in dichloromethane).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4872a28e89749d2811406cee1fac057
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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