Water → HCID 21397385, Verbindung

HRID 1439476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1439476
[H-].[Na+].[C:3]1([CH:9]([CH2:13][CH2:14][CH2:15][CH:16]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:10](=[O:12])[CH3:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].O>C1C=CC=CC=1.CN(C)C=O.CCOCC>[C:10]([C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([CH2:13][CH2:14][CH2:15][CH:16]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])(=[O:12])[CH3:11]

Komponenten

8

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoateHCID 213973967-(Benzyloxy)-3-phenyldodecan-2-one

Produkt 1

HCID 21397385HCID 21397385, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (0.8 g., 0.033 mole) is suspended in a mixture of benzene (50 ml.) and dimethylformamide (50 ml.) and 3-phenyl-7-benzyloxy-2-dodecanone (12.1 g., 0.033 mole) is added dropwise. The resulting mixture is heated on the steam bath for 1 hour and then cooled to room temperature. Ethyl 7-bromoheptanoate (8.8 g., 0.037 mole) is added dropwise and the mixture is heated on the steam bath for 24 hours. The reaction mixture is cooled, poured into water (200 ml.) and the oily product taken up in ether and dried over sodium sulfate. The solvent is distilled in vacuo to leave 14 g. of ethyl 8-acetyl-8-phenyl-12-benzyloxyheptadecanoate as a yellow oil which is used in Step G without further purification.

Aufarbeitung

  1. additionis added dropwise
  2. temperatureThe resulting mixture is heated on the steam bath for 1 hour
  3. temperaturethe mixture is heated on the steam bath for 24 hours
  4. temperatureThe reaction mixture is cooled
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent is distilled in vacuo
  7. customto leave 14 g
  8. customof ethyl 8-acetyl-8-phenyl-12-benzyloxyheptadecanoate as a yellow oil which is used in Step G without further purification

Quellen und Nachweise

ORD-Eintrag
ord-3692ac771bed448f8905ee27fd8c5127
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04059601

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