Methyl iodide → Heptanoic acid, 6-oxo-, methyl ester

HRID 628940Notes

Reaction equation

HRID 628940 reaction equation
N12CCCN=C1CCCC[CH2:2]2.[O:12]=[C:13]([CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].IC>CC(C)=O>[O:12]=[C:13]([CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:2])=[O:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 988106-Oxoheptanoic acid

Product 1

HCID 288022Heptanoic acid, 6-oxo-, methyl esterYield 97.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (3.4 mL, 22.86 mmol) was added to a solution of 6-oxoheptanoic acid 23 (1.1 g, 7.63 mmol) in acetone (15 mL) at 23° C. After stirring for 15 min iodomethane (2.4 mL, 38.3 mmol) was added. The reaction was stirred for 1 h and then the solvent was removed in vacuo. The residue was purified by flash column chromatography (silica gel, 7:3 hex/EtOAc) to provide 1.18 g (95%) of the methyl ester 24 (see scheme 4).

Workup

  1. additionwas added
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by flash column chromatography (silica gel, 7:3 hex/EtOAc)

Sources & evidence

ORD record
ord-07fb0fa9b4c94e7a93d0aed4974726bd
Source dataset
uspto-grants-2016_04
Patent number
US09315486B2

Reaction notes

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