Triethylamine → 1,2-Dilinoleyl-3-methanesulfonylglycerol

HRID 1473834Notes

Reaction equation

HRID 1473834 reaction equation
[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]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58264329HCID 58264329, compound

Product 1

HCID 866690811,2-Dilinoleyl-3-methanesulfonylglycerol

Conditions

Temperature
-15 °C

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-b90f3f0cc90d47468af388e600a9f4b0
Source dataset
uspto-grants-2015_04
Patent number
US09018187B2

Reaction notes

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