Dimethyl Sulfoxide → 4-(2,3-Epoxypropoxy)-1-octyloxy-2,2,6,6-tetramethylpiperidine

HRID 1900287Notes

Reaction equation

HRID 1900287 reaction equation
[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[N:5]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:4]([CH3:20])([CH3:19])[CH2:3]1.[H-].[Na+].CS(C)=O.[CH2:27]([CH:29]1[O:31][CH2:30]1)Cl>O1CCCC1>[CH2:11]([O:10][N:5]1[C:6]([CH3:8])([CH3:9])[CH2:7][CH:2]([O:1][CH2:27][CH:29]2[O:31][CH2:30]2)[CH2:3][C:4]1([CH3:19])[CH3:20])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 113466831-Octyloxy-2,2,6,6-tetramethylpiperidin-4-ol

Product 1

HCID 539867304-(2,3-Epoxypropoxy)-1-octyloxy-2,2,6,6-tetramethylpiperidineYield 16.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 20.0 grams (70 mmol) of 4-hydroxy-1-octyloxy-2,2,6,6-tetramethylpiperidine (prepared in Example 5), 1.68 gram (70 mmol) of sodium hydride, 2 ml of dimethyl sulfoxide, and 150 ml of tetrahydrofuran is heated at reflux for three hours. The reaction mixture is cooled to room temperature, and a solution of 6.5 grams (70 mmol) of epichlorohydrin in 50 ml of tetrahydrofuran is added over a 5-minute period. The reaction mixture is stirred sixteen hours at room temperature and then partitioned between ether and water. The aqueous layer is extracted with ether and the combined ether solutions are dried over anhydrous magnesium sulfate before concentrating to yield an oil. Purification by flash chromatography (4:1 hexane:ethyl acetate) affords 3.9 grams (16% yield) of the title compound as a colorless oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux for three hours
  3. custompartitioned between ether and water
  4. extractionThe aqueous layer is extracted with ether
  5. dry with materialthe combined ether solutions are dried over anhydrous magnesium sulfate
  6. concentrationbefore concentrating
  7. customto yield an oil
  8. customPurification by flash chromatography (4:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-2213d661fbb14e0aa73f6008852c8d19
Source dataset
uspto-grants-1996_11
Patent number
US05574162

Reaction notes

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