Methanol → 1-Methoxy-2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene
Reaction equation
[CH3:1][C:2](=[CH:5][CH:6]=[C:7]([CH3:24])[CH:8]=[CH:9][CH:10]=[C:11]([CH3:23])[CH:12]=[CH:13][C:14]1[C:19]([CH3:21])([CH3:20])[CH2:18][CH2:17][CH2:16][C:15]=1[CH3:22])[CH2:3][OH:4].[CH:25](OC)(OC)OC.CO.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:25][O:4][CH2:3][C:2]([CH3:1])=[CH:5][CH:6]=[C:7]([CH3:24])[CH:8]=[CH:9][CH:10]=[C:11]([CH3:23])[CH:12]=[CH:13][C:14]1[C:19]([CH3:21])([CH3:20])[CH2:18][CH2:17][CH2:16][C:15]=1[CH3:22]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene-1-ol (1.6 g, 5 mmol), 1.06 g (10 mmol) of trimethyl orthoformate and 160 mg (5 mmol) of dry methanol in 5 ml of dry THF is added dropwise a solution of 40 μL of trifluoroacetic acid in 1 ml of dry THF over a 1 minute period at room temperature. After overnight standing, the reaction mixture is poured into cold aqueous 5% NaHCO3 and extracted with chloroform three times. The combined organic extract is washed with water, dried over Na2SO4 and evaporated in vacuo to give a residue, which is purified by HPLC (4% ether in hexane, silica gel column) to afford of 1-methoxy-2,5,9-trimethyl-11-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8,10-undecapentaene as an oil.
Workup
- extractionextracted with chloroform three times
- extractionThe combined organic extract
- washis washed with water
- dry with materialdried over Na2SO4
- customevaporated in vacuo
- customto give a residue, which
- customis purified by HPLC (4% ether in hexane, silica gel column)
Sources & evidence
- ORD record
- ord-c83ce741b17b43029cb1f089d1308426
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04523042
Reaction notes
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