Hydrochloric Acid → (2R, 4 R)-2-{(4-octyloxybenzoyloxy)phenyl)-4-decanolide

HRID 346086

Reaktionsgleichung

Reaktionsgleichung von HRID 346086
O[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][C@@H:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[O:11][C:9]2=[O:10])=[CH:4][CH:3]=1.[CH2:20]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].N1C=CC=CC=1.Cl.CC[O:47]CC>ClCCl>[CH2:20]([O:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([O:47][C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=2[C@H:8]2[CH2:13][C@@H:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[O:11][C:9]2=[O:10])=[O:34])=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 3283Diethyl EtherHCID 27602504-Octyloxybenzoyl chlorideHCID 15653390(2R,4R)-2-(4-hydroxyphenyl)-4-decanolide

Produkt 1

HCID 131717046(2R, 4 R)-2-{(4-octyloxybenzoyloxy)phenyl)-4-decanolideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 4 ml of dichloromethane were dissolved 50 mg of (2R,4R)-2-(4-hydroxyphenyl)-4-decanolide obtained in Example 3 and 49 mg of 4-octyloxybenzoyl chloride. To this solution was added 1 ml of pyridine. The resulting mixture was stirred for 6 hours under heating to reflux. The reaction mixture was allowed to cool, and then 50 ml of ether and diluted hydrochloric acid were added thereto. The resulting organic layer was separated, washed with water, and then dried with anhydrous sodium sulfate. The solvent was removed by evaporation and the resulting crude produce was purified by silica gel column chromatography, thereby obtaining 65 mg of crystals of the desired compound (yield 70%).

Aufarbeitung

  1. temperatureunder heating to reflux
  2. temperatureto cool
  3. customThe resulting organic layer was separated
  4. washwashed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe resulting crude produce
  8. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b894cfc4840f4b88a6acd51b9015b5da
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05061398

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