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

HRID 502942
Notes
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Reaction equation

HRID 502942 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2777567Methyl 3-chloro-4-methylthiophene-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 59767697(3-Chloro-4-methylthiophen-2-yl)methanolYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. stirringthe whole was stirred at room temperature for 1 hour
  2. filtrationThe solution was filtered
  3. additionafter ethyl acetate was added
  4. customthe organic layer was separated
  5. washFurthermore, the organic layer washed with brine
  6. dry with materialafter drying over anhydrous sodium sulfate and filtration
  7. customthe solvent was removed by evaporation under reduced pressure
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes