Lithium Hydroxide → HCID 19979111, compound

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).

1. washwashed with brine (100 mL)
2. dry with materialThe organics were dried over MgSO4
3. customevaporated to dryness
4. additionThe residue was diluted with THF (5 mL) and MeOH (2 mL)
5. stirringThe reaction mixture was stirred for 18 h
6. customthe solvents were removed under vacuum
7. extractionThe product was extracted into EA (30 mL)
8. washwashed with water (100 mL)
9. customThe organics were pre-absorbed onto silica gel
10. custompurified by chromatography (EA/isohexanes)

ORD record

ord-47d681ba3e3f46989a7206468a3c0e83

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278910B2