Acetyl chloride → 1-(2,3-Dihydro-benzo[b]thiophen-5-yl)-ethanone

HRID 546256

Reaktionsgleichung

[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[C:10](Cl)(=[O:12])[CH3:11].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([C:10](=[O:12])[CH3:11])[CH:8]=[CH:9][C:2]1=2

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

To a solution of 2,3-dihydro-benzo[b]thiophene (1.88 g, 13.8 mmol) in methylene chloride (20 mL) at −10° C. was added dropwise a solution of acetyl chloride (1.85 mL, 25.9 mmol) and aluminum chloride (1.84 g, 13.8 mmol) in methylene chloride (20 mL) keeping the temperature below −6° C. during the addition period. After the addition is complete the reaction mixture was stirred for an additional 30 min at −10° C. and then added ice (40 mL) and concentrated hydrochloric acid (6 mL) and extracted with methylene chloride (3×20 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification on an AnaLogix Intelliflash system (80 g column, 10% diethyl ether/hexanes) afforded 1-(2,3-dihydro-benzo[b]thiophen-5-yl)-ethanone (1.93 g, 78%) as a clear colorless oil.

Aufarbeitung

customthe temperature below −6° C.
additionduring the addition period
additionAfter the addition
extractionadded ice (40 mL) and concentrated hydrochloric acid (6 mL) and extracted with methylene chloride (3×20 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification on an AnaLogix Intelliflash system (80 g column, 10% diethyl ether/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-81945bebadd143538357f16eee7e0bfe
Quelldatensatz: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07935699B2

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