Aluminium lithium hydride → HCID 90418164, compound

HRID 2177330Notes

Reaction equation

HRID 2177330 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[CH:13]=[O:14])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[CH2:13][OH:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 82392097HCID 82392097, compound

Product 1

HCID 90418164HCID 90418164, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Into a 250-mL round-bottom flask, was placed a solution of 3-(4-chlorophenyl)thiophene-2-carbaldehyde (5.5 g, 24.70 mmol, 1.00 equiv) in tetrahydrofuran (50 ml). This was followed by the addition of LAH (470 mg, 12.38 mmol, 1.00 equiv) in several batches at −10° C. The resulting solution was stirred for 30 min at −10° C. The reaction was then quenched by the addition of 5 g of sodium sulfate. 10H2O. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with PE/EA (30/1-1/1). This resulted in 5 g (81%) of [3-(4-chlorophenyl)thiophen-2-yl]methanol as a white solid.

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 5 g of sodium sulfate
  3. filtrationThe solids were filtered out
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. customThis resulted in 5 g (81%) of [3-(4-chlorophenyl)thiophen-2-yl]methanol as a white solid

Sources & evidence

ORD record
ord-74f44b4b60314fbda73ac599d049d5f8
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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