Lithium Hydroxide → HCID 19979111, compound

Participants

Reaction Steps

To a stirring solution of heptan-1-ol (0.84 ml, 5.93 mmol) in THF (10 mL) at 0° C. was added sodium hydride (0.25 g, 6.20 mmol, 60 wt % suspension in mineral oil). The reaction mixture was allowed to warm to room temperature. After 1 h, a solution of ethyl 6-chloronicotinate (1.00 g, 5.39 mmol) in THF (5 mL) was added and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with EA (50 mL) and washed with brine (100 mL). The organics were dried over MgSO4 and evaporated to dryness. The residue was diluted with THF (5 mL) and MeOH (2 mL) then 1 N lithium hydroxide (1.08 mL, 1.08 mmol) was added. The reaction mixture was stirred for 18 h. The reaction mixture was acidified by the addition of acetic acid (to pH 5) and the solvents were removed under vacuum. The product was extracted into EA (30 mL) and washed with water (100 mL). The organics were pre-absorbed onto silica gel and purified by chromatography (EA/isohexanes) to afford 131 mg (10%) of 6-(heptyloxy)nicotinic acid INT-11 as a white powder. LCMS-ESI (m/z) calculated for C13H19NO3: 237; found 238 [M+H]+, tR=2.52 min (Method 10).

Provenance & Evidence