Dimethyl Sulfoxide → ethyl 5-[tert-butyl(dimethyl)silyl]oxypent-2-enoate
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([Si:15]([CH3:22])([CH3:21])[O:16][CH2:17][CH2:18][CH2:19]O)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.[CH2:30]([O:32][C:33]([CH:35]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:34])[CH3:31]>ClCCl>[Si:15]([O:16][CH2:17][CH2:18][CH:19]=[CH:35][C:33]([O:32][CH2:30][CH3:31])=[O:34])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:22])[CH3:21]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl sulphoxide (1.9 ml, 26.8 mmol) was added to a cooled (−78° C.) solution of oxalyl chloride (2.16 ml, 24.7 mmol) in dichloromethane (100 ml), and after 10 minutes, a solution of 3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol (3 g, 15.8 mmol) in dichloromethane (25 ml) was added dropwise. Once addition was complete, the solution was stirred for a further 15 minutes. Triethylamine (8 ml, 57.5 mmol) was added, followed by dropwise addition of a solution of (ethoxycarbonylmethylene)triphenylphosphorane (10 g, 29.9 mmol) in dichloromethane (50 ml), and the reaction mixture allowed to warm to room temperature. The mixture was washed with water (4×), dried (MgSO4) and concentrated under reduced pressure. The residue was pre-adsorbed onto silica gel and purified by column chromatography using diethyl ether:pentane (2.5:97.5) as eluant to afford the title compound, 1.3 g; 1H NMR (CDCl3, 400 MHz) δ: 0.02 (s, 6H), 0.87 (s, 9H), 1.26 (t, 3H), 2.40 (m, 2H), 3.74 (t, 2H), 4.18 (q, 2H), 5.84 (d, 1H), 6.95 (m, 1H).
Workup
- additionOnce addition
- washThe mixture was washed with water (4×)
- dry with materialdried (MgSO4)
- concentrationconcentrated under reduced pressure
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-af167df68b9548059e9822dd060e4cff
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07045653B2
Reaction notes
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