Acetyl chloride → HCID 22143532, Verbindung

HRID 1825067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1825067
[C:1](Cl)(=[O:3])[CH3:2].CCN(CC)CC.[OH:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19]([CH3:21])[S:18][C:17]=2[CH:22]=1>C1COCC1.CCOC(C)=O>[C:1]([O:12][C:13]1[CH:14]=[CH:15][C:16]2[CH:20]=[C:19]([CH3:21])[S:18][C:17]=2[CH:22]=1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 122034952-Methyl-1-benzothiophen-6-OL

Produkt 1

HCID 22143532HCID 22143532, VerbindungAusbeute 126,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Acetyl chloride (1.5 ml, 1.66 g, 21 mmole) and Et3N (3 ml, 2.18 g, 21.5 mmole) were added, sequentially, to a solution of 6-hydroxy-2-methylbenzo[b]thiophene 8a (2.51 g, 15 mmole) in THF (120 ml) at 0°. The reaction was left stirring for 14 hours, gradually warming to ambient temperature, then diluted with EtOAc (100 ml) and washed with H2O (100 ml) and brine (100 ml). The combined aqueous layers were extracted with EtOAc (100 ml). The combined organic extracts were subsequently dried over Na2SO4 and concentrated, in vacuo, to give 3.9 g of a yellow solid which was purified by silica gel chromatography. Elution with hexane: Et2O (90:10) and evaporation of the appropriate fractions gave 2.93 g (93%) of a white solid. 1H NMR (DMSO-d6) δ 7.70 (1H, d, J=8.6 Hz), 7.66 (1H, d, J=2.2 Hz), 7.12 (1H, s), 7.07 (1H, dd, J=2.2, 8.6 Hz), 2.54 (3H, s), 2.27 (3H, s). Anal. Calcd. for C, 11H10O2S: C, 64.05; H, 4.89; S, 15.55. Found: C, 63.84; H, 4.93; S, 15.57.

Aufarbeitung

  1. customat 0°
  2. waitThe reaction was left
  3. washwashed with H2O (100 ml) and brine (100 ml)
  4. extractionThe combined aqueous layers were extracted with EtOAc (100 ml)
  5. dry with materialThe combined organic extracts were subsequently dried over Na2SO4
  6. concentrationconcentrated, in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7f2cadeb978342f1a8fca01c46193ad3
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07045528B2

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