Dimethyl Sulfoxide → 3,7,11,15-Tetramethylhexadec-2-enal
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][CH:12]([CH2:14][CH2:15][CH2:16][C@H:17]([CH2:19][CH2:20][CH2:21][C@H:22]([CH2:24][CH2:25][CH2:26]/[C:27](=[CH:29]/[CH2:30][OH:31])/[CH3:28])[CH3:23])[CH3:18])[CH3:13].C(N(CC)CC)C>C(Cl)Cl>[CH3:28][C:27]([CH2:26][CH2:25][CH2:24][CH:22]([CH3:23])[CH2:21][CH2:20][CH2:19][CH:17]([CH3:18])[CH2:16][CH2:15][CH2:14][CH:12]([CH3:13])[CH3:11])=[CH:29][CH:30]=[O:31]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Under a nitrogen atmosphere, 17.4 mL (202 mmol) of oxalyl chloride was dissolved in methylene chloride (300 mL). 36 mL (0.51 mol) of dimethyl sulfoxide was slowly added dropwise to the mixture at −78° C. After the mixture was stirred for 15 min, 50 g (0.17 mol) of phytol was added, followed by stirring for 1 hour at the same temperature. After addition of 94 mL (0.68 mol) of triethylamine, the reaction mixture was allowed to warm up to room temperature. The mixture was concentrated with methylene chloride, and the residue was diluted with diethylether, and the solution was washed saturated brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated to obtain 3,7,11,15-tetramethylhexadec-2-en-1-al as a crude product.
Workup
- stirringby stirring for 1 hour at the same temperature
- concentrationThe mixture was concentrated with methylene chloride
- additionthe residue was diluted with diethylether
- washthe solution was washed saturated brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationAfter filtration
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-e372cf8b45cf45038dfb2617d4e1f4b5
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703922B2
Reaction notes
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