Acetamide → Methyl 6-benzoyloxyhexanoate

HRID 1197232

Reaction equation

HRID 1197232 reaction equation
[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14](Br)[C:15]([O:17][CH3:18])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:20].[K+].C(N)(=O)C>>[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([F:20])[C:15]([O:17][CH3:18])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 522689Potassium FluorideHCID 15222235methyl 6-benzoyloxy-2(RS)-bromohexanoate

Product 2

HCID 15224608methyl 6-benzoyloxy-2(RS)-fluorohexanoateHCID 19930972Methyl 6-benzoyloxyhexanoateYield 58.3%

Conditions

Temperature
105 °C

Procedure

A mixture of methyl 6-benzoyloxy-2(RS)-bromohexanoate (e) (14.02 g), potassium fluoride (12.59 g) and acetamide (12.3 g) was stirred at 105° C. for 6 hours. The crude product obtained by treating in the conventional manner was subjected to silica gel chromatography to give the title compound (f) and methyl 6-benzoyloxyhexanoate (g) (3.11 g, yield: 29%). Yield: 5.28 g (46%)

Workup

  1. customThe crude product obtained
  2. additionby treating in the conventional manner

Sources & evidence

ORD record
ord-7c1c1f17e99e46ce86c0edbb36248acc
Source dataset
uspto-grants-1992_05
Patent number
US05117042

Linked notes

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