Pyridine → 1,3-Cyclopentanedione, 2,2-dimethyl-
Reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][C:4](=[O:7])[C:3]1([CH3:9])[CH3:8].N1C=CC=CC=1.CO[C@](C1C=CC=CC=1)(C(F)(F)F)C(Cl)=O>ClC(Cl)C>[CH3:8][C:3]1([CH3:9])[C:2](=[O:1])[CH2:6][CH2:5][C:4]1=[O:7]Participants
5
Procedure
The enantiomeric excess of 3 was assayed by 1H NMR of the corresponding Mosher's ester which was prepared by treatment of alcohol 3 (11 mg, 0.09 mmol) in dichloroethane (0.3 mL, Aldrich) with pyridine (27 μL, 0.33 mmol, Aldrich) and (R)-α-methoxy-α-trifluoromethyphenylacetic acid chloride (58 μL, 0.31 mmol, Fluka). The mixture was stirred overnight and then partitioned between water (10 mL) and ether (10 mL). The ether layer was washed with 1 M HCl (10 mL) and saturated NaHCO3 solution and then was dried (MgSO4), filtered and evaporated. 1H NMR analysis was done on the crude ester.
Workup
- custompartitioned between water (10 mL) and ether (10 mL)
- washThe ether layer was washed with 1 M HCl (10 mL) and saturated NaHCO3 solution
- dry with materialwas dried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-cab47265739043a8a3a22ba362e99cec
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855226B2
Reaction notes
Loading…