Tetrabutylammonium Fluoride → HCID 11345161, compound

HRID 1180792Notes

Reaction equation

HRID 1180792 reaction equation
[Si]([O:8][CH2:9][C:10]1([CH2:14][CH2:15][S:16][C:17]2[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=2)[CH2:13][CH2:12][CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:22][N:18]1[CH:19]=[CH:20][N:21]=[C:17]1[S:16][CH2:15][CH2:14][C:10]1([CH2:9][OH:8])[CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 11313824HCID 11313824, compound

Product 1

HCID 11345161HCID 11345161, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1.39 g (4.1 mmol) of 2-({2-[1-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclobutyl]ethyl}sulfanyl)-1-methyl-1H-imidazole in 10 mL of tetrahydrofuran was added a 1.0 M solution of 4.92 mL (5.33 mmol) of tetrabutylammonium fluoride in tetrahydrofuran and the contents stirred for 16 h. The reaction was concentrated and the residue was poured directly onto a column of silica gel eluting with ethyl acetate:hexane to afford 0.57 g (62%) of (1-{2-[(1-methyl-1H-imidazol-2-yl)sulfanyl]ethyl}cyclobutyl)methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 6.94 (s, 1H), 6.82 (s, 1H), 5.30 (br s, 1H), 3.66 (s, 2H), 3.47 (s, 3H), 2.94 (m, 2H),1.99-1.64 (m, 8H).

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe residue was poured directly onto a column of silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-68d17d2dcdad45aca04288a14a34c186
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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