Methyl iodide → HCID 20313171, compound

HRID 839723Notes

Reaction equation

HRID 839723 reaction equation
[CH2:1]([Li])CCC.C(NC(C)C)(C)C.[C:13]1([CH:19]2[CH2:22][CH:21]([C:23]([O:25][CH3:26])=[O:24])[CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CI>CCCCCC.O1CCCC1>[CH3:1][C:21]1([C:23]([O:25][CH3:26])=[O:24])[CH2:20][CH:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:22]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 20313170HCID 20313170, compoundHCID 178418339Butyllithium

Product 1

HCID 20313171HCID 20313171, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyl lithium (8.15ml. of a 1.23M solution in hexane) was added dropwise to a stirred solution of di-isopropylamine (1.40ml.) in dry tetrahydrofuran (15ml.) at -78° C. in an atmosphere of argon. The solution was warmed to 0° C. and a solution of methyl 3-phenylcyclobutanecarboxylate (1.90g.) in dry tetrahydrofuran (20ml.) was added dropwise and the reaction mixture was stirred at 0° C. for 1 hour. Methyl iodide (1.30ml.) was added and stirring was continued for 16 hours, allowing the reaction mixture to warm to room temperature. The tetrahydrofuran was evaporated under reduced pressure and the residue was partitioned between ethyl acetate (2 × 20ml.) and 0.5N hydrochloric acid (10ml.). The ethyl acetate solution was dried over sodium sulphate and the solvent was evaporated under reduced pressure to give the ester, methyl 1-methyl-3-phenylcyclobutanecarboxylate as a 2:1 mixture of isomers. The n.m.r. spectrum is deuteriochloroform showed the following characteristic features (δ values):

Workup

  1. stirringstirring
  2. waitwas continued for 16 hours
  3. temperatureto warm to room temperature
  4. customThe tetrahydrofuran was evaporated under reduced pressure
  5. customthe residue was partitioned between ethyl acetate (2 × 20ml.) and 0.5N hydrochloric acid (10ml.)
  6. dry with materialThe ethyl acetate solution was dried over sodium sulphate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ed07d0fd95d34d7b94035a7e0d9fdec6
Source dataset
uspto-grants-1978_06
Patent number
US04096337

Reaction notes

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