Citric Acid → HCID 18630236, compound
Reaction equation
[Li][CH:2](CC)C.C1CCCCC1.CN(CCN(C)C)C.[CH3:20][C:21]([N:24]([CH3:38])[C:25](=[O:37])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[Si:33]([CH3:36])([CH3:35])[CH3:34])([CH3:23])[CH3:22].CI.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:23][C:21]([N:24]([CH3:38])[C:25](=[O:37])[C:26]1[C:31]([CH3:2])=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[Si:33]([CH3:34])([CH3:35])[CH3:36])([CH3:20])[CH3:22]Participants
8
Conditions
- Temperature
- -100 °C
Procedure
1.3M s-BuLi in cyclohexane (31.4 mL, 41 mmol) was added dropwise to THF (100 mL) and TMEDA (5.35 g, 46 mmol), cooled to -100° C. under nitrogen with stirring. To this mixture was added dropwise the compound of Example 5 (10.45 g, 37 mmol), dissolved in a minimum amount of THF. After stirring for 10 min, MeI (15.8 g, 0.1114 mol) was injected. The mixture was stirred for 1 h and 25% citric acid (15 mL) was added. The mixture was extracted three times with ether; the ether extracts were combined and washed twice with water, dried (MgSO4), and concentrated. The crude product was purified by RC, with 1:9 ethyl acetate/hexanes. The title compound was recovered as a light yellow solid, in 99% yield. m.p. 44°-47° C.
Workup
- stirringAfter stirring for 10 min
- stirringThe mixture was stirred for 1 h
- extractionThe mixture was extracted three times with ether
- washwashed twice with water
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe crude product was purified by RC, with 1:9 ethyl acetate/hexanes
- customThe title compound was recovered as a light yellow solid, in 99% yield
Sources & evidence
- ORD record
- ord-bfd7911815834cdab6beba96c0e443f8
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849723
Reaction notes
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