Methyl iodide → HCID 20313171, compound

HRID 2420140Notes

Reaction equation

HRID 2420140 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 in 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-686c214200364f3795b0794c6bd7cd4c
Source dataset
uspto-grants-1978_08
Patent number
US04109015

Reaction notes

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