Sodium hydride → HCID 19099907, compound

HRID 1885702Notes

Reaction equation

HRID 1885702 reaction equation
[H-].[Na+].[CH2:3]([O:11][N:12]1[C:17]([CH3:19])([CH3:18])[CH2:16][CH:15]([O:20][CH2:21][CH:22]2[O:24][CH2:23]2)[CH2:14][C:13]1([CH3:26])[CH3:25])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[OH:27][CH:28]1[CH2:33][C:32]([CH3:35])([CH3:34])[N:31]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:30]([CH3:46])([CH3:45])[CH2:29]1>O1CCOCC1.C(OCC)C>[CH2:37]([O:36][N:31]1[C:32]([CH3:34])([CH3:35])[CH2:33][CH:28]([O:27][CH2:23][CH:22]([OH:24])[CH2:21][O:20][CH:15]2[CH2:14][C:13]([CH3:25])([CH3:26])[N:12]([O:11][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:17]([CH3:18])([CH3:19])[CH2:16]2)[CH2:29][C:30]1([CH3:45])[CH3:46])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Participants

6

Reactant 3

HCID 24758Sodium hydride2×HCID 113466831-Octyloxy-2,2,6,6-tetramethylpiperidin-4-olHCID 539867304-(2,3-Epoxypropoxy)-1-octyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 19099907HCID 19099907, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Sodium hydride (0.7 g. 5.9 mmol) is added to a solution of 17.0 g (59.5 mmol) of 1-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yloxy)-2,3-epoxypropane (prepared in Example 11) in 75 ml of dioxane. The reaction mixture is heated at reflux for 10 minutes and then cooled to 60° C., whereupon a solution of 10.0 g (29.3 mmol) of 4-hydroxy-1-octyloxy-2,2,6,6-tetramethylpiperidine (prepared in Example 5) in 25 ml of dioxane is rapidly added. The reaction mixture is heated at reflux for 4 hours, treated with an additional 0.6 g of sodium hydride, and heated at reflux for 7 hours. The reaction mixture is diluted with diethyl ether (500 ml), and the organic solution is washed with 1N hydrochloric acid (2×100 ml) and saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated to an oil. Purification by flash chromatography on silica gel (9:1 heptane: ethyl acetate) affords 8.4 g (46% yield) of the title compound, a colorless oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 10 minutes
  3. additionis rapidly added
  4. temperatureThe reaction mixture is heated
  5. temperatureat reflux for 4 hours
  6. temperatureheated
  7. temperatureat reflux for 7 hours
  8. washthe organic solution is washed with 1N hydrochloric acid (2×100 ml) and saturated sodium bicarbonate solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated to an oil
  11. customPurification by flash chromatography on silica gel (9:1 heptane: ethyl acetate)

Sources & evidence

ORD record
ord-6d1ebb005faf4c3d9031c4f74144bfb9
Source dataset
uspto-grants-1992_09
Patent number
US05145893

Reaction notes

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