Hydrochloric Acid → (3-Chloro-4-methylthiophen-2-yl)methanol

HRID 502942Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[C:14](OC)=[O:15].Cl>C1COCC1>[Cl:7][C:8]1[C:12]([CH3:13])=[CH:11][S:10][C:9]=1[CH2:14][OH:15]

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (1.35 g) was added to a THF (50 ml) solution of methyl 3-chloro-4-methylthiophene-2-carboxylate (3.40 g) at 0° C., followed by stirring at 0° C. for 20 minutes. An 1M aqueous hydrochloric acid solution was added to the reaction solution and the whole was stirred at room temperature for 1 hour. The solution was filtered and, after ethyl acetate was added, the organic layer was separated. Furthermore, the organic layer washed with brine and, after drying over anhydrous sodium sulfate and filtration, the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by column chromatography (hexane:ethyl acetate=4:1) to obtain 2.68 g of (3-chloro-4-methyl-2-thienyl)methanol (pale yellow oil).

Workup

stirringthe whole was stirred at room temperature for 1 hour
filtrationThe solution was filtered
additionafter ethyl acetate was added
customthe organic layer was separated
washFurthermore, the organic layer washed with brine
dry with materialafter drying over anhydrous sodium sulfate and filtration
customthe solvent was removed by evaporation under reduced pressure
customThe resulting crude product was purified by column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-10c891dbc6f84eb99077cbf9ea87afca
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07776897B2

Reaction notes

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