Ammonium Chloride → 3-Methylbenzo(b)thiophene-2-methanol

HRID 241357Notes

Reaction equation

HRID 241357 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[C:17](OC)=[O:18].[Cl-].[NH4+]>C1COCC1>[CH3:7][C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[CH2:17][OH:18]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 268658Methyl 3-methylbenzo[b]thiophene-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 6012933-Methylbenzo(b)thiophene-2-methanolYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cold suspension of lithium aluminum hydride (103 mg, 2.72 mmol) in THF (4.4 mL) was added dropwise over 15 minutes under N2 atmosphere, a solution of the above-mentioned methyl 3-methylbenzothiophene-2-carboxylate (560 mg, 2.72 mmol) in THF (1 mL). The mixture was stirred under ice-cooling for 45 minutes, then at room temperature for 5 minutes, to which was added dropwise under ice-cooling saturated aqueous ammonium chloride solution. The mixture was filtered through a layer of Celite, washed with ethyl acetate. Combined organic layers were washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to give the titled compound as a white crystal (483 mg, yield 99%).

Workup

  1. additionwas added dropwise over 15 minutes under N2 atmosphere
  2. temperaturecooling for 45 minutes
  3. additionto which was added dropwise under ice-
  4. filtrationThe mixture was filtered through a layer of Celite
  5. washwashed with ethyl acetate
  6. washCombined organic layers were washed with saturated brine
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c4e41246410b4364bfc9e143838fb2ab
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

Loading…