Iodoethane → HCID 12398830, compound

HRID 1283672Notes

Reaction equation

HRID 1283672 reaction equation
[CH2:1]([Li])[CH2:2]CC.C(NC(C)C)(C)C.[O:13]=[C:14]1[C:20]2[CH:21]=[CH:22][C:23]([CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:19]=2[CH:18]=[CH:17][C:16]2[CH:30]=[CH:31][CH:32]=[CH:33][C:15]1=2.C(I)C>CCCCCC.CO.O.CCOCC.CN(C)P(=O)(N(C)C)N(C)C.O1CCCC1>[O:13]=[C:14]1[C:20]2[CH:21]=[CH:22][C:23]([CH:25]([CH2:1][CH3:2])[C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:19]=2[CH:18]=[CH:17][C:16]2[CH:30]=[CH:31][CH:32]=[CH:33][C:15]1=2

Participants

11

Reactant 4

HCID 6340Iodoethane3×HCID 7912DiisopropylamineHCID 12398824HCID 12398824, compoundHCID 178418339Butyllithium

Product 1

HCID 12398830HCID 12398830, compound

Reagents, catalysts & solvents 6

HCID 887MethanolCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-60 °C

Procedure

1.075 Ml. of 1.6 molar n-butyllithium in hexane is added to a solution of 0.242 ml. of diisopropylamine in 15 ml. of dry tetrahydrofuran. 0.300 Ml. of hexamethylphosphoric triamide is added and the mixture is cooled to about -60°C. 0.465 G. of methyl (5-oxo-5H-dibenzo[a,d] cyclohepten-2-yl)acetate is added, and after 15 minutes, 0.137 ml. of ethyl iodide is added. The mixture is warmed slowly to room temperature and a further 0.05 ml. of ethyl iodide is added. After 30 minutes an additional 0.05 ml. of ethyl iodide is added. After 30 minutes, a few drops of methanol are added, and then ether and water are added. The organic layer is washed with water, dilute hydrochloric acid and saturated sodium chloride solution, then dried and evaporated to yield the impure product, which, after chromatography on 40 g. silica gel, eluting with hexane:ether (5:1) affords methyl 2-(5-oxo-5H-dibenzo-[a,d]cyclohepten-2-yl)butyrate. 0.326 G. of methyl 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)butyrate is refluxed for 4 hours in 10 ml. of methanol and 20 ml. of water containing 0.5 g. of sodium hydroxide. The mixture is cooled, washed with ether and acidifed with dilute hydrochloric acid. The product is extracted with ether and the extract washed, dried and evaporated to yield 2-(5-oxo-5H-dibenzo[a,d]cyclohepten-2-yl)butyric acid (m.p. 147°-148°C).

Workup

  1. temperatureThe mixture is warmed slowly to room temperature
  2. waitAfter 30 minutes an additional 0.05 ml
  3. waitAfter 30 minutes
  4. washThe organic layer is washed with water, dilute hydrochloric acid and saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customto yield the impure product, which
  8. washsilica gel, eluting with hexane:ether (5:1)

Sources & evidence

ORD record
ord-e5b431a192094f3db44db40fcff84ad0
Source dataset
uspto-grants-1976_08
Patent number
US03975540

Reaction notes

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