Triethylamine → 6-{2-[2-(2-{2-[2-(2-Methylsulfonylethoxy) ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl ester

HRID 24990Notes

Reaction equation

HRID 24990 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27]O)[CH3:2].C(N(CC)CC)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][S:38]([CH3:37])(=[O:40])=[O:39])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 865870286-{2-[2-(2-{2-[2-(2-Hydroxyethoxy)ethoxy]ethoxy}-ethoxy)ethoxy]-ethoxy}-hexanoic acid ethyl ester

Product 1

HCID 865870276-{2-[2-(2-{2-[2-(2-Methylsulfonylethoxy) ethoxy]ethoxy}-ethoxy)-ethoxy]-ethoxy}-hexanoic acid ethyl esterYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The non-polydispersed alcohol 19 (0.835 g, 1.97 mmol) was dissolved in 3.5 ml dry dichloromethane and placed under a nitrogen atmosphere. Triethylamine (0.301 ml, 0.219 g, 2.16 mmol) was added and the mixture was chilled in an ice bath. After two minutes, the methanesulfonyl chloride (0.16 ml, 0.248 g, 2.16 mmol) was added. The mixture was stirred for 15 minutes at 0° C., then at room temperature for two hours. The reaction mixture was filtered through silica gel to remove the triethylammonium chloride, and the filtrate was washed successively with water, saturated NaHCO3, water and brine. The organics were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 9/1 ethyl acetate/methanol) to give non-polydispersed compound 20 as a clear oil (0.819 g, 83%). FAB MS: m/e 503 (M+H).

Workup

  1. temperaturethe mixture was chilled in an ice bath
  2. waitat room temperature for two hours
  3. filtrationThe reaction mixture was filtered through silica gel
  4. customto remove the triethylammonium chloride
  5. washthe filtrate was washed successively with water, saturated NaHCO3, water and brine
  6. dry with materialThe organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (silica gel, 9/1 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-2672324b43b54ccb8310c1539dd2f7a1
Source dataset
uspto-grants-2005_02
Patent number
US06858580B2

Reaction notes

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