Acetate → HCID 15864468, compound
Reaction equation
[C:1]([O:4][CH:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH3:6])(=[O:3])[CH3:2].C([O-])(=O)C.CC(O)CCCCCCC>C1C=CC=CC=1>[C:1]([O:4][C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH2:6])(=[O:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
This reaction was performed as in Example 1 with bis(cyclooctadienyl)rhodium tetrafluoroborate (10 mg; 0.025 mmol; 0.01 equiv), R,R-1,2-bis(2,5-dimethylphospholano)benzene (6, R"=CH3 ; 9 mg; 0.03 mmol; 0.012 equiv) and non-1-en-2-yl acetate (461 mg; 2.5 mmol) in 10 mL of degassed THF until hydrogen uptake ceased (2 h) to afford 0.46 g of crude product. 1H NMR analysis indicated 2-nonyl acetate as the sole product, and chiral GC analysis and comparison to racemate indicated 64.0% ee for 2-nonyl acetate. Hydrolysis of the acetate to 2-nonanol and comparison of the optical rotation, [α]D24 -13.9° (c 1.15, benzene), with the literature value for the (S) enantiomer, [α]D18 +11.4° (c 1.30, benzene) (Mori, K.; Ogita, H. Leibigs Ann. Chem. 1994, 1065.), indicated the (R) configuration for 2-nonyl acetate.
Sources & evidence
- ORD record
- ord-beba69fd723049d483bc7ec046c323db
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05886214
Reaction notes
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