Triethylamine → 1,2-Dilinoleyl-3-methanesulfonylglycerol

HRID 1473834ノート

反応式

HRID 1473834 の反応式
[CH2:1]([O:19][CH2:20][CH:21]([CH2:41][OH:42])[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(N(CC)CC)C.[S:50](Cl)([CH3:53])(=[O:52])=[O:51]>>[CH2:1]([O:19][CH2:20][CH:21]([CH2:41][O:42][S:50]([CH3:53])(=[O:52])=[O:51])[O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

4

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58264329HCID 58264329、化合物

生成物 1

HCID 866690811,2-Dilinoleyl-3-methanesulfonylglycerol

反応条件

温度
-15 °C

実験手順

1,2-Dilinoleylglycerol (26) (11.0 g, 18.7 mmol), triethylamine (5.04 mL, 36 mmol), and a stir bar were added to a 250 mL round bottom flask. The flask was sealed and flushed with nitrogen. Anhydrous DCM (75 mL) was added, and the mixture cooled to −15° C. (Ice and NaCl). Mesyl Chloride (2.80 mL, 36 mmol) was added via syringe over a 5 minute period, and the reaction stirred at −15° C. for 1 hour. At this point TLC showed that the starting material had been consumed. The solution was diluted with DCM (120 mL) and washed with saturated NaHCO3 (2×150 mL). The organic phase was then dried (MgSO4), filtered, concentrated, and the product purified by column chromatography (10.6 g, 85%).

後処理

  1. customThe flask was sealed
  2. customflushed with nitrogen
  3. additionAnhydrous DCM (75 mL) was added
  4. customhad been consumed
  5. additionThe solution was diluted with DCM (120 mL)
  6. washwashed with saturated NaHCO3 (2×150 mL)
  7. dry with materialThe organic phase was then dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe product purified by column chromatography (10.6 g, 85%)

出典と根拠

ORDレコード
ord-b90f3f0cc90d47468af388e600a9f4b0
出典データセット
uspto-grants-2015_04
特許番号
US09018187B2

反応ノート

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