Hydrochloric Acid → HCID 11379265, compound

HRID 864717Notes

Reaction equation

HRID 864717 reaction equation
CSC.[C:4]1([Mg]Br)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13]1.C([C:21]([O:23][CH3:24])=[O:22])#N.Cl>C1COCC1.C(OCC)C.CN(C)P(N(C)C)(N(C)C)=O>[C:4]1([CH:14]2[CH2:15][CH2:16][CH2:17][C:12](=[O:18])[CH:13]2[C:21]([O:23][CH3:24])=[O:22])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 135942-Cyclohexen-1-oneHCID 28660Carbonocyanidic acid, methyl esterHCID 178418255HCID 178418255, compound

Product 1

HCID 11379265HCID 11379265, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 6.0 g (0.03 mol) of cuprous iodide in 100 ml of THF was added 25 ml of dimethyl sulfide, and the resulting yellow solution was cooled to -78° C. and treated dropwise with a solution of 23 ml (0.06 mol) of a 3.0M solution of phenyl magnesium bromide in diethyl ether. The resulting pale yellow-orange solution was stirred at -78° C. under nitrogen for one hour and then treated with 3.02 g (0.03mol) of 2-cyclohexenone in 10 ml of THF. The resulting mixture was allowed to warm to 0° C. over a two hour period, recooled to -78° C. treated with 15 ml of hexamethylphosphoramide, stirred for thirty minutes, treated with 8.0 g (0.09 mol) of methyl cyanoformate and allowed to warm to ambient temperature overnight. The reaction mixture was poured into 100 ml of 2N hydrochloric acid, and the organic phase was separated and the aqueous phase back-extracted with MDC. The combined organic extracts were taken to dryness in vacuo and the residue triturated with saturated ammonium chloride, then with water, then with brine and taken to dryness once again to give 3.2 g of methyl 2-phenylcyclohexan-6-one carboxylate as an oil.

Workup

  1. temperatureto warm to 0° C. over a two hour period
  2. customrecooled to -78° C.
  3. stirringstirred for thirty minutes
  4. temperatureto warm to ambient temperature overnight
  5. customthe organic phase was separated
  6. extractionthe aqueous phase back-extracted with MDC
  7. customthe residue triturated with saturated ammonium chloride

Sources & evidence

ORD record
ord-22a4ec9fa67e4158ae97a7225c1c1c62
Source dataset
uspto-grants-1996_10
Patent number
US05563163

Reaction notes

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