Tetrabutylammonium Fluoride → HCID 57455399, compound

HRID 521253Notes

Reaction equation

HRID 521253 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][O:22][Si](C(C)(C)C)(C)C)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 12106184HCID 12106184, compound

Product 1

HCID 57455399HCID 57455399, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 2-butyl-1-[4-(tert-butyldimethylsilanyloxy)butyl]-1H-imidazo[4,5-c]quinoline from the previous step and tetrabutylammonium fluoride (142 mL of a 1 M solution in tetrahydrofuran) were dissolved in tetrahydrofuran (THF) (400 mL) and stirred for 1 hour, then concentrated under reduced pressure to provide 4-(2-butyl-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-6403ab43d28d4740903e7b7a1b4452f7
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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