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

HRID 1708625노트

반응식

HRID 1708625 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d3f14a16f49146d8977ddd5914662c5d
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05359069

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