Triethylamine → HCID 131731342, compound
Reaction equation
C(N(CC)CC)C.[O:8]=[C:9]1[O:15][C@H:14]([C@H:16]([CH2:18][OH:19])[OH:17])[C:12]([OH:13])=[C:10]1[OH:11].[CH3:20][C:21]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:51])[CH2:40][CH2:41][CH2:42][CH:43]([CH3:50])[CH2:44][CH2:45][CH2:46][CH:47]([CH3:49])[CH3:48])=[CH:22][CH2:23][CH2:24]OS(C1C=CC(C)=CC=1)(=O)=O>C(#N)C>[CH3:20][C:21]([CH2:36][CH2:37][CH2:38][CH:39]([CH3:51])[CH2:40][CH2:41][CH2:42][CH:43]([CH3:50])[CH2:44][CH2:45][CH2:46][CH:47]([CH3:49])[CH3:48])=[CH:22][CH2:23][CH2:24][O:11][C:10]1[C:9]([O:15][C@H:14]([C@H:16]([CH2:18][OH:19])[OH:17])[C:12]=1[OH:13])=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
0.49 mL (3.5 mmol) of triethylamine was added and dissolved in a suspension of 0.56 g (3.2 mmol) of ascorbic acid in acetonitrile (7 mL). After the above crude product of (4,8,12,16-tetramethylheptadec-3-enyl)tosylate was added at room temperature, the reaction mixture was heated for 2 hours at 90° C. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (methanol/methylene chloride mixture) to obtain the title compound.
Workup
- concentrationThe reaction mixture was concentrated
- customthe resulting residue was purified by silica gel column chromatography (methanol/methylene chloride mixture)
Sources & evidence
- ORD record
- ord-fc2eb04c09f243eab5f9bfe1c6c678d1
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703922B2
Reaction notes
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