Triethylamine → Methyl dihydrojasmonate, cis-(+)-
Reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[C:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH2:16](N(CC)CC)C.[H][H]>C1COCC1.CO>[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][C:8]([O:10][CH3:16])=[O:9])[C@@H:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]Participants
Procedure
To a solution of 252 mg (1.20 mmole) 3-oxo-2-pentyl-1 cyclopentene-1-acetic acid, in a mixture of 7 ml of THF and 21 ml of methanol, there were added 2 ml of the catalyst solution obtained in a) (0.025 mmole, 0.021 eq.) and 10.4 μl of triethylamine (0.075 mmole, 3 eq.) under stirring at r.t. This solution, prepared in the glass container of a standard autoclave, was introduced in this autoclave, which was locked, put under a pressure of 45×105Pa of hydrogen and stirred at r.t. The reaction was followed by gas chromatography and was completed in about 4 h. After 1 night, the contents were evaporated under vacuum at r.t., the residue taken in ether, washed with HCl 10.1N and then water, dried over MgSO4 and filtered. The thus obtained (+)-(1R)-3-oxo-2-pentyl-1-cyclopentaneacetic acid was esterified by means of diazomethane to yield methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate, the chromatographic analysis (GC) of which indicated 97% purity, 96:4 cis/trans ratio and 95:5 (+)-(1R)-cis/(-)-(1S)-cis ratio.
Workup
- customThis solution, prepared in the glass container of a standard autoclave
- additionwas introduced in this autoclave, which
- stirringstirred at r.t
- waitAfter 1 night
- customthe contents were evaporated under vacuum at r.t.
- washwashed with HCl 10.1N
- dry with materialwater, dried over MgSO4
- filtrationfiltered
Sources & evidence
- ORD record
- ord-c559e57f319541fc972edd30a8da1304
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05728866
Reaction notes
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