Ethyl acetate hexane → 1-Pyridine-4-yl-2-m-tolyl-ethane-1,2-diol

HRID 566717Notes

Reaction equation

HRID 566717 reaction equation
C([Si](C)(C)[O:6][CH:7]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[CH:8]([C:10]1[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=1)[OH:9])(C)(C)C.[F-].C([NH3+])(C)(C)C.CCCCCC.C(OCC)(=O)C>C1COCC1>[N:20]1[CH:21]=[CH:22][C:17]([CH:7]([OH:6])[CH:8]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)[OH:9])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 212665272-(Tert-butyl-dimethyl-silanyloxy)-2-pyridine-4-yl-1-m-tolyl-ethanolHCID 21866379t-Butylammonium fluoride

Product 1

HCID 212664901-Pyridine-4-yl-2-m-tolyl-ethane-1,2-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(tert-butyl-dimethyl-silanyloxy)-2-pyridine-4-yl-1-m-tolyl-ethanol (5 g, 14.5 mmole) in THF (50 mL) was added t-butylamonium fluoride (1M, 16 mL, 16 mmole) at 25° C. The solution was stirred at that temperature for 1 hr before evaporation of solvent and purification (silica gel, hexane/ethyl acetate) to give the title compound. MS (m/z): Calcd. C14H15NO2(M+): 229, found (M+H)+: 230.1, (M−H)−: 228.1

Sources & evidence

ORD record
ord-9be82ae3919947fc8b1fb53b6d0d7730
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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