1-Iodohexane → 3-(4-Benzyloxyphenyl)-2-hexyloxypropanoic acid methyl ester

HRID 987241Notes

Reaction equation

HRID 987241 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([OH:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[CH2:22](I)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>ClCCl.[Ag-]=O>[CH3:1][O:2][C:3](=[O:21])[CH:4]([O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 125271-IodohexaneHCID 10493427Methyl 3-[4-(benzyloxy)phenyl]-2-hydroxypropanoate

Product 1

HCID 545196553-(4-Benzyloxyphenyl)-2-hexyloxypropanoic acid methyl esterYield 87.4%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3-(4-Benzyloxyphenyl)-2-hydroxypropanoic acid methyl ester (0.4243 g; 1.482 mmole) was dissolved in dry dichloromethane (10 ml). Silver (I) oxide (1.717 g; 7.41 mmole) was added, followed by slow addition of hexyl iodide (0.943 g; 4.45 mmole). The reaction mixture was stirred at room temperature for 3 hours then molecular sieves (3 Å) was added and the reaction mixture was stirred for 4 more days and then filtered. The solvent was evaporated and evacuation at 60° C. for 5 hours gave 0.48 g (87% yield) of 3-(4-benzyloxyphenyl)-2-hexyloxypropanoic acid methyl ester.

Workup

  1. additionmolecular sieves (3 Å) was added
  2. stirringthe reaction mixture was stirred for 4 more days
  3. filtrationfiltered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ec1cce0200354ec7bd63a3c4ba682848
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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