Tetrabutylammonium Fluoride → HCID 86605563, compound

HRID 1819951Notes

Reaction equation

HRID 1819951 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:18]2[S:22][C:21]([S:23]([OH:26])(=[O:25])=[O:24])=[C:20]([CH3:27])[CH:19]=2)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:9][C:8]=1[CH3:28])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:14]([C:13]([C:18]1[S:22][C:21]([S:23]([OH:26])(=[O:25])=[O:24])=[C:20]([CH3:27])[CH:19]=1)([C:10]1[CH:11]=[CH:12][C:7]([OH:6])=[C:8]([CH3:28])[CH:9]=1)[CH2:16][CH3:17])[CH3:15]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86605562HCID 86605562, compound

Product 1

HCID 86605563HCID 86605563, compoundYield 111.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 5-{1-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-1-ethyl-propyl}-3-methyl-thiophene-2-sulfonic acid dimethylaminemethyleneamide (6.1 g, 11.68 mmol) in THF (150 ml) is added dropwise tetrabutylammonium fluoride (15.62 ml, 15.62 mmol, 1.0 M in THF) and is warmed to RT for 1 h. The reaction is quenched with satd aqueous NH4Cl (100 ml) and extracted with Et2O (2×200 ml). The combined organic layers are dried MgSO4 dried, concentrated and chromatographed (120 g SiO2, 50% EtOAc/Hex) to yield the title compound (4.63 g, 97%).

Workup

  1. customThe reaction is quenched with satd aqueous NH4Cl (100 ml)
  2. extractionextracted with Et2O (2×200 ml)
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed (120 g SiO2, 50% EtOAc/Hex)

Sources & evidence

ORD record
ord-cf215d5ae9b44ec69be6c8a0664af439
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

Loading…