Triethylamine → 1,2-Dilinoleyl-3-methanesulfonylglycerol

HRID 1045337노트

반응식

HRID 1045337 반응식
[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]

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58264329HCID 58264329, 화합물

생성물 1

HCID 866690811,2-Dilinoleyl-3-methanesulfonylglycerol

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온도
-15 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-61f2cbb75a7f4f1ab53f6f45b009c845
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569256B2

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