Tetrabutylammonium Fluoride → 5-(3-(2-Hydroxyethyl)benzyl)-3-isobutoxycyclopent-2-enone
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:23][C:24]1[CH2:28][CH:27]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][CH2:37][O:38][Si](C(C)C)(C(C)C)C(C)C)[CH:31]=2)[C:26](=[O:49])[CH:25]=1)[CH:20]([CH3:22])[CH3:21]>O1CCCC1>[OH:38][CH2:37][CH2:36][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=1)[CH2:29][CH:27]1[C:26](=[O:49])[CH:25]=[C:24]([O:23][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:28]1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A solution of tetrabutylammonium fluoride (1 M in tetrahydrofuran, 0.47 mL, 0.47 mmol) was added dropwise to an ice-water bath cooled solution of 20 (0.071 g, 0.16 mmol) in anhydrous tetrahydrofuran (1 mL). The reaction mixture was stirred at 0° C. for 3 h and then quenched with a saturated solution of ammonium chloride. The two phases were separated and the aqueous layer was extracted with diethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by silica gel column chromatography using dichloromethane-methanol 95:5 as eluent to provide the desired product as colorless oil.
Workup
- customquenched with a saturated solution of ammonium chloride
- customThe two phases were separated
- extractionthe aqueous layer was extracted with diethyl ether
- washThe combined organic layers were washed with brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-7d2bf8746c5b4c22b06a6bed937bb015
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530520B2
Reaction notes
Loading…