Dimethyl Sulfoxide → HCID 19008668, compound
Reaction equation
[OH:1][CH2:2][C:3]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][O:4]1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].CS(C)=O.[OH-].[K+]>[Cl-].[Na+].O.O1CCCC1>[CH2:28]([O:1][CH2:2][C:3]1([CH2:8][OH:9])[CH2:7][CH2:6][CH2:5][O:4]1)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]Participants
Procedure
To a mixture of 2.64 g (0.002 mol) of 2,2-bis(hydroxymethyl)-tetrahydrofuran and 2.2 g (0.0066 mol) of bromooctadecane in 8 ml of 1:1 mixture of dimethylsulfoxide and tetrahydrofuran was added 1.84 g (0.0264 mol) of finely powdered potassium hydroxide. The resultant mixture was then stirred at room temperature for 2 hours, after which time it was poured onto 100 ml of water, diluted with 20 ml of an aqueous saturated sodium chloride solution and extracted with ether. The ether extract was then washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate and the ether was removed under reduced pressure. The crude product was then purified by column chromatography on silica gel employing a mixture of methyl-t-butyl ether and hexane (3:1 ratio) as the eluent to yield the desired compound as a wax.
Workup
- extractionextracted with ether
- extractionThe ether extract
- washwas then washed with an aqueous saturated sodium chloride solution
- dry with materialdried over anhydrous sodium sulfate
- customthe ether was removed under reduced pressure
- customThe crude product was then purified by column chromatography on silica gel employing
- additiona mixture of methyl-t-butyl ether and hexane (3:1 ratio) as the eluent
Sources & evidence
- ORD record
- ord-82a9c89abba1438eaf54b72189cf684d
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04673672
Reaction notes
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