Potassium Carbonate → HCID 54074476, compound
Reaction equation
Cl[CH2:2][C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])=[CH2:4].ClCC(C)=CCC=C(C)C.[CH3:21][C:22]([C:29]#[CH:30])=[CH:23][CH2:24][CH2:25][C:26](=[O:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[CH3:21][C:22]([C:29]#[C:30][CH2:2][C:3]([CH3:4])=[CH:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])=[CH:23][CH2:24][CH2:25][C:26](=[O:28])[CH3:27]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The coupling reaction was conducted in the manner described in the procedure of Example XVIII using the following reagents: 162 mg (1.02 mmoles) of a mixture of 2-chloromethyl-6-methyl-1,5-heptadiene and 1-chloro-2,6-dimethyl-2,5-heptadiene (produced in accordance with Example XXI), 138 mg (1.01 mmoles) of 6-methyl-5-octen-7-yn-2-one (produced in accordance with Example II), 232 mg (1.68 mmoles) of anhydrous potassium carbonate, 9 mg (0.09 mmole) of cuprous chloride, and 20 mg (0.088 mmole) of benzyltriethylammonium chloride in 1.00 mL of acetonitrile (HPLC-grade). Isolation of the product in the manner described in the procedure of Example III afforded 242 mg (93% yield) of material, shown by proton NMR analysis to contain a minor amount (approximately 25%) of unreacted starting ketone and allylic chlorides. Fractional evaporative distillation afforded 136 mg (52% yield, not corrected for recovery of starting materials) of the named unsaturated C-18 ketones: boiling point 115°-128° C. (bath temperature, 0.20 mm). The identity of this product mixture was confirmed by high-field (300 MHz) proton NMR analysis.
Workup
- customThe coupling reaction
Sources & evidence
- ORD record
- ord-cb156b1f4aaa449cb9151441dadb19b7
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05231232
Reaction notes
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