Hydrochloric Acid → HCID 14989158, compound
Reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[CH3:24][Li].Cl>O1CCCC1>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([S:16][CH2:17][CH2:18][C:19]([OH:23])([CH3:24])[CH:20]([CH3:21])[CH3:22])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -50 °C
Procedure
40 ml of tetrahydrofuran was added to a flask that had been dried overnight at 100° C. in vacuo and 4.5 g (0.0134 mole) of the ketone of Example 12 was added. All processes were done under an argon atmosphere. The solution was cooled to about -50° C. in a dry ice/acetone bath and 19.16 ml (0.0268 mole) of 1.4M methyl lithium in tetrahydrofuran was added dropwise maintaining the temperature to about -60° C. to -50° C. When addition was complete, the reaction mixture was warmed to about 0° C. and 1N hydrochloric acid was added. The reaction mixture was extracted three times with ethyl acetate, the extracts combined, washed with water twice, dried over sodium sulfate, filtered and the solvent removed in vacuo. The residue was chromatographed on silica to give the title compound identical with that of Example 15.
Workup
- additionwas added
- temperaturemaintaining the temperature to about -60° C. to -50° C
- additionWhen addition
- temperaturethe reaction mixture was warmed to about 0° C.
- extractionThe reaction mixture was extracted three times with ethyl acetate
- washwashed with water twice
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customthe solvent removed in vacuo
- customThe residue was chromatographed on silica
Sources & evidence
- ORD record
- ord-6b990a8fd7664f408497f11b1c032f04
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04857558
Reaction notes
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