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

HRID 1708625ノート

反応式

HRID 1708625 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d3f14a16f49146d8977ddd5914662c5d
出典データセット
uspto-grants-1994_10
特許番号
US05359069

反応ノート

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