(S)-2,6-Dimethyl-undec-2-ene → (S)-4-methylnonanoic acid
Reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@@H:7]([CH3:13])CCCCC)[CH3:3].C[C:15]([CH3:17])=[O:16].[OH:18]S(O)(=O)=O.O=[Cr](=O)=O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>CC(C)=O>[CH3:1][C@@H:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:13])[CH2:3][CH2:17][C:15]([OH:18])=[O:16]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Compound 162 (7.97 g, 43.7 mmol) was dissolved in acetone (214 mL) and cooled to 0° C. Jones reagent (CrO3/H2SO4) (2.7 M, 95 mL) was added dropwise, and the reaction allowed to warm to room temperature over 18 hours. The reaction was poured on to water/Na2SO4 (200 mL), and the aqueous layer extracted with ethyl acetate (4×100 mL). The combined organics were dried over MgSO4, filtered, and rotovapped to give an oil. The crude oil was chromatographed on silica eluting with hexanes to give 163 as an oil (5.56 g, 74%). 1H NMR (400 MHz, CDCl3) δ 2.40–2.25 (m, 4H), 1.70–1.62 (m, 2H), 1.47–1.11 (m, 8H), 0.87–0.84 (m, 6H); MS APCI m/z 170.9 (M−1, 100%).
Workup
- temperatureto warm to room temperature over 18 hours
- extractionthe aqueous layer extracted with ethyl acetate (4×100 mL)
- dry with materialThe combined organics were dried over MgSO4
- filtrationfiltered
- customto give an oil
- customThe crude oil was chromatographed on silica eluting with hexanes
Sources & evidence
- ORD record
- ord-11f882ae01164c7e97e6ca33503cd3c4
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07138542B2
Reaction notes
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