Diethyl Ether → HCID 90418719, compound

HRID 2177350Notes

Reaction equation

HRID 2177350 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[CH:12][C:13]=2[C:14](O)=[O:15])=[CH:5][CH:4]=1)[CH3:2].CCOCC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:10][CH:11]=[CH:12][C:13]=2[CH2:14][OH:15])=[CH:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 22754844HCID 22754844, compound

Product 1

HCID 90418719HCID 90418719, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a 100-mL 3-necked round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed 2-(4-ethylphenyl)thiophene-3-carboxylic acid (0.46 g, 1.98 mmol), anhydrous ether (18 mL). This was followed by the addition of a solution of LiAlH4 (1 M in THF, 2.7 mL, 2.7 mmol) in tetrahydrofuran dropwise with stirring at 0° C. The resulting solution was stirred for 2.0 h at 25° C. The reaction progress was monitored by LCMS/TLC (ethyl acetate/petroleum ether=1:6). The reaction was then quenched by the addition of 10 mL of water and 5 mL of 2N HCl. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4). This resulted in 0.46 g (100%) of (2-(4-ethylphenyl)thiophen-3-yl)methanol as a white oil.

Workup

  1. customInto a 100-mL 3-necked round-bottom flask (1 atm) purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred for 2.0 h at 25° C
  4. customThe reaction was then quenched by the addition of 10 mL of water and 5 mL of 2N HCl
  5. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 0.46 g (100%) of (2-(4-ethylphenyl)thiophen-3-yl)methanol as a white oil

Sources & evidence

ORD record
ord-e99f0225fb5c40d9a0fa934173b14717
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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