1-Iodopropane → methyl (S)-3-(4-bromophenyl)-2-(propyloxy)propanoate

HRID 1009224Notes

Reaction equation

HRID 1009224 reaction equation
[CH2:1](I)[CH2:2][CH3:3].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([OH:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1>C(OCC)C.[Ag]=O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([O:18][CH2:1][CH2:2][CH3:3])[C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 336431-IodopropaneHCID 39359925methyl (S)-3-(4-bromophenyl)-2-hydroxypropionate

Product 1

HCID 67305005methyl (S)-3-(4-bromophenyl)-2-(propyloxy)propanoateYield 83.3%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

0.22 ml (2.31 mmol) of propyl iodide is added to a mixture of 793 mg (3.48 mmol) of silver oxide and 300 mg (1.16 mmol) of methyl (S)-3-(4-bromophenyl)-2-hydroxypropionate in 3 ml of diethyl ether. The reaction mixture is stirred at 50° C. for 12 hours. The mixture is filtered and then the solvents are evaporated. The residue is chromatographed on silica gel (heptane/ethyl acetate 80/20). 291 mg of methyl (S)-3-(4-bromophenyl)-2-(propyloxy)propanoate are obtained in the form of an oil. Yield=83%.

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvents are evaporated
  3. customThe residue is chromatographed on silica gel (heptane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-86b2a595b123496d88d1a40999e7bcd0
Source dataset
uspto-grants-2011_07
Patent number
US07973063B2

Reaction notes

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