Cyclohexanol → HCID 86600139, compound

HRID 1983571Notes

Reaction equation

HRID 1983571 reaction equation
O[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH:12]1([OH:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH2:16]1[CH2:17][CH:12]([O:18][C:5]2[N:4]=[CH:3][CH:2]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 354317Methyl 5-hydroxypyridine-3-carboxylate

Product 1

HCID 86600139HCID 86600139, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 5-hydroxynicotinate (2.40 g, 15.7 mmol) in methylene chloride (40 mL) was added cyclohexanol (1.73 g, 1.80 mL, 17.2 mmol) and triphenylphosphine (5.75 g, 21.9 mmol). The solution was treated with diethyl azodicarboxylate (3.20 mL, 20.4 mmol), resulting in a mild exotherm and development of an orange colored solution. The reaction mixture was allowed to stir at room temperature. After 16 hours, the cloudy yellow suspension was filtered, and the filtrate was washed with saturated sodium bicarbonate solution and brine, dried (magnesium sulfate), filtered, and concentrated to provide a yellow oil. Flash chromatography over silica (hexanes/ethyl acetate) afforded 1.08 g (29%) of the desired product as a colorless oil: 1H NMR (CDCl3) δ 8.77 (d, J=1.7 Hz, 1H), 8.43 (d, J=2.9 Hz, 1H), 7.74 (dd, J=1.7, 2.9 Hz, 1H), 4.37-4.31 (m, 1H), 3.94 (s, 3H), 2.01-1.93 (m, 2H), 1.85-1.75 (m, 2H), 1.62-1.49 (m, 3H), 1.46-1.31 (m, 3H) ppm. 13C NMR (CDCl3) δ 166.2, 154.0, 144.2, 142.9, 126.6, 122.3, 76.3, 52.7, 31.6, 25.6, 23.7 ppm.

Workup

  1. customresulting in a mild exotherm and development of an orange colored solution
  2. filtrationthe cloudy yellow suspension was filtered
  3. washthe filtrate was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a yellow oil

Sources & evidence

ORD record
ord-88dfed52781f4d9ab03d86e5114de40c
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

Loading…