HCID 20389689, compound → HCID 22808737, compound
Reaction equation
I/[CH:2]=[CH:3]/[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C([Li])(C)(C)C.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[C:25](=[O:29])[CH2:26][CH2:27][CH:28]=1.C(O)(=O)C.O.C1COCC1>CCOCC.CCCCC.C#CCCC.[Cu+]>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C@@H:24]1[C@@H:28](/[CH:2]=[CH:3]/[CH2:4][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:27][CH2:26][C:25]1=[O:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 1.13 gm of 1-iodo-3-cyclohexyl-1-transpropene (4.50 mmol) in 22 ml dry ether was cooled to -78° with stirring under argon and treated with 8.60 ml of 1.07 M t-butyllithium in pentane. The reaction mixture was stirred for 2 hours at -78°, and transferred into a stirred, -78° solution of 532 mg of copper(I)pentyne in 12 ml dry ether (solubilized at 25° by addition of 1.50 ml hexamethylphosphorus triamide). The resultant complex was stirred for 0.5 hour at 1.0 gm (3.86 mmol) of the material prepared in Example XVI in 4.5 ml dry ether was injected dropwise over 10 minutes. The reaction mixture was stirred for 0.5 hours at -78°, 1.5 hours at -10° and 0.5 hour at 0°. The reaction mixture was processed as described, infra, in Example XVIII, excluding the treatment with acetic acid/water/THF to yield 1.55 gm of a yellow oil. Chromatography (85:15 silicic acid-Celite, benzene→ethyl acetate gradient elution) afforded 1.19 gm of a yellow oil, Rf (system II) 0.58.
Workup
- stirringThe reaction mixture was stirred for 2 hours at -78°
- stirringThe reaction mixture was stirred for 0.5 hours at -78°, 1.5 hours at -10° and 0.5 hour at 0°
Sources & evidence
- ORD record
- ord-64016984065b48cebbe4e91ea3df0cf2
- Source dataset
- uspto-grants-1979_10
- Patent number
- US04171331
Reaction notes
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