Methyl chloroformate → HCID 59642988, compound

HRID 2251613Notes

Reaction equation

HRID 2251613 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)([CH3:3])[CH3:2].[Li]CCCC.Cl[C:22]([O:24][CH3:25])=[O:23].CCOC(C)=O>C1COCC1.CCCCCC>[CH:1]([C:4]1[CH:5]=[C:6]([O:14][CH3:15])[C:7]([O:10][CH2:11][O:12][CH3:13])=[C:8]([CH:9]=1)[C:22]([O:24][CH3:25])=[O:23])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8857Ethyl AcetateHCID 59643052HCID 59643052, compoundHCID 178418339Butyllithium

Product 1

HCID 59642988HCID 59642988, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-isopropyl-2-methoxy-1-methoxymethoxy-benzene (2.0 g, 9.51 mmol) in 35 mL dry THF cooled to 0° C., BuLi (9 mL of a 1.6 m solution in hexane, 1.5 eq.) was added dropwise via a syringe and the reaction mixture was stirred 2.5 h at 0° C. This solution was then slowly added to a solution of methyl chloroformate (9 g, 95.1 mmol, 10 eq.) in 10 mL dry THF at 0° C. The mixture was stirred 12 h at r.t. Saturated KHCO3 solution and EtOAc were then added to the solution and the phases were separated. The organic layer was washed twice with saturated NaCl solution, dried over MgSO4 and evaporated in vacuo. The crude product was purified using flash chromatography (silica gel, hexane EtOAc 9:1→6:1) to yield the title compound as a yellowish oil.

Workup

  1. stirringThe mixture was stirred 12 h at r.t
  2. customthe phases were separated
  3. washThe organic layer was washed twice with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-06770eb2a49744f09793e9ad4f5a18dd
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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