Diethyl Ether → HCID 11744855, compound
Reaction equation
[CH2:1]([CH:5]1[CH2:10][CH2:9][CH:8]=[CH:7][C:6]1=O)[CH2:2][CH2:3][CH3:4].CC[O:14]CC>>[CH2:1]([C@@H:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:14])[CH2:6]1)[CH2:2][CH2:3][CH3:4]Participants
Procedure
Prepared according to the general procedure from 3-butylcyclohexen-2-one (168 mg, 1.09 mmol) in 0.2 M Et2O for 43 h at room temperature to provide the title compound as a colorless oil (128.3 mg, 75% yield, 88% ee) after purification by flash chromatography on silica gel (5% Et2O/pentane). The physical data were identical in all respects to those previously reported (Jones et al. (1998). Tetrahedron 54:1471; and Moritani et al. (2000), J. Am. Chem. Soc. 122:6797 (reported a rotation of −17° for the (S)-enantiomer that is 87% ee)). The enantiomeric ratio was determined by GLC using a Hydrodex-B-TBDAc (50 m×0.25 mm) column (150° C. isotherm, 1 mL/min.); (S) isomer tr=37.0 min. and (R) isomer tr=36.0 min. [α]D22=+15.5° (c=1.00, CHCl3).
Workup
- customPrepared
Sources & evidence
- ORD record
- ord-3f2ea6edfe594e3796352001ee61e815
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07323604B2
Reaction notes
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