Reaction equation
[CH3:1][C:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:21])[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)=[CH:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7].[CH:22]([Mg]Br)=[CH2:23].[Cl-].[NH4+]>O1CCCC1>[CH3:7][C:6]([OH:8])([CH2:5][CH2:4][CH:3]=[C:2]([CH3:1])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:21])[CH2:13][O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[CH:22]=[CH2:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (80 mg, 0.27 mmol) in tetrahydrofuran (3 ml) was stirred on an ice bath under argon atmosphere. To the solution was added vinylmagnesium bromide in tetrahydrofuran (0.3 ml, 0.3 mmol, 1.0 M), and the mixture was warmed to room temperature and stirred for 10 hours. After addition of saturated aqueous ammonium chloride (2 ml), the reaction mixture was extracted with ether. The extract was dried over Na2SO4 and evaporated in vacuo to remove the solvent to give a crude product, which was purified with silica gel column chromatography to obtain 3,7,11-trimethyl-12-(2-tetrahydropyranyl)oxy-1,6,10-dodecatrien-3-ol (61 mg, 70%). IR(film)cm-1 ; 3460, 2950, 2880, 1200, 1118, 1075, 1022, 905, 865, 810.
Workup
- extractionthe reaction mixture was extracted with ether
- dry with materialThe extract was dried over Na2SO4
- customevaporated in vacuo
- customto remove the solvent
- customto give a crude product, which
- customwas purified with silica gel column chromatography
Sources & evidence
- ORD record
- ord-040d953b7c4342fe86b15659471a5179
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05245085
Linked notes
Loading…