Triethylamine → 4-(1-Monofluoro-2-decyloxycarbonyl)phenyl 4-octyloxybenzoate

HRID 247781

Reaktionsgleichung

Reaktionsgleichung von HRID 247781
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([O:8][CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][F:11])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:29]([O:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>C(Cl)Cl.O>[CH2:29]([O:37][C:38]1[CH:39]=[CH:40][C:41]([C:42]([O:1][C:2]2[CH:21]=[CH:20][C:5]([C:6]([O:8][CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][F:11])=[O:7])=[CH:4][CH:3]=2)=[O:43])=[CH:45][CH:46]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 27602504-Octyloxybenzoyl chlorideHCID 190138911-Monofluoro-2-decyl 4-hydroxybenzoate2×

Produkt 1

HCID 190139064-(1-Monofluoro-2-decyloxycarbonyl)phenyl 4-octyloxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of the 1-monofluoro-2-decyl 4-hydroxybenzoate prepared in (1) (0.1 g) and triethylamine (0.04 g) in methylene chloride (10 ml) was slowly added under ice cooling a solution of 4-n-octyloxybenzoic acid chloride (0.1 g) in methylene chloride (10 ml). The mixture was left to stand until it reached room temperature and stirred overnight. The mixture was poured in water and extracted with methylene chloride. The extracted layer was washed with dilute aqueous hydrochloric acid solution, water, 1N aqueous sodium carbonate solution and water, in this order, and dehydrated over anhydrous magnesium sulfate. After the solution was distilled under reduced pressure to remove the solvent, the product was purified by silica-gel column chromatography to obtain the titled compound (0.13 g).

Aufarbeitung

  1. waitThe mixture was left
  2. customreached room temperature
  3. extractionextracted with methylene chloride
  4. washThe extracted layer was washed with dilute aqueous hydrochloric acid solution, water, 1N aqueous sodium carbonate solution and water, in this order
  5. distillationAfter the solution was distilled under reduced pressure
  6. customto remove the solvent
  7. customthe product was purified by silica-gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0a33a91ca3894683ad8fb3ad64b66b95
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05207947

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