p-Toluenesulfonic acid monohydrate → tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one
Reaction equation
C([C@H](C(O)CC([O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1)CCCCCCCCCCC)C(O)=O)CCCCC.[OH2:33].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37](S(O)(=O)=O)=[CH:36][CH:35]=1>C(O)C>[OH:33][C@@H:31]1[CH2:30][CH2:29][CH:28]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:34][CH3:44])[O:27][C:26]1=[O:25]Participants
4
Procedure
M)a) 15.4 g of a diastereomer mixture of 2-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid were dissolved in 160 ml of ethanol and 800 mg of toluene-4-sulfonic acid monohydrate were added. The reaction mixture was heated to 55°-60° C. until the reaction was finished. The solvent was removed in vacuo and the residue was dissolved in 160 ml of dichloromethane. The solution was stirred at room temperature for 1 hour. The reaction mixture was evaporated. The material obtained was chromatographed on silica gel. There was obtained tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one, m.p. 95°-96° C.
Workup
- temperatureThe reaction mixture was heated to 55°-60° C. until the reaction
- customThe solvent was removed in vacuo
- dissolutionthe residue was dissolved in 160 ml of dichloromethane
- customThe reaction mixture was evaporated
- customThe material obtained
- customwas chromatographed on silica gel
Sources & evidence
- ORD record
- ord-79667b592cd94ca2943c996933ceac25
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05246960
Reaction notes
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