Aluminium lithium hydride → HCID 90418125, compound

HRID 2177366Notes

Reaction equation

HRID 2177366 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH3:22])=[C:11]([C:18]([F:21])([F:20])[F:19])[C:12]=2[C:13](OCC)=[O:14])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH3:22])=[C:11]([C:18]([F:21])([F:19])[F:20])[C:12]=2[CH2:13][OH:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90418489HCID 90418489, compound

Product 1

HCID 90418125HCID 90418125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Into a 100-mL round-bottom flask, was placed ethyl 2-(4-chlorophenyl)-5-methyl-4-(trifluoromethyl)thiophene-3-carboxylate (200 mg, 0.57 mmol, 1.00 equiv), tetrahydrofuran (20 mL). This was followed by the addition of LAH (44 mg, 1.16 mmol, 2.02 equiv) in several batches at 0° C. The resulting solution was stirred for 2 h at 25° C. The reaction was then quenched by the addition of 1 g of Na2SO4.10H2O. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/5). The collected fractions were combined and concentrated under vacuum. This resulted in 80 mg (43%) of (5-methyl-2-phenyl-4-(trifluoromethyl)thiophen-3-yl)methanol as light yellow oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customThe reaction was then quenched by the addition of 1 g of Na2SO4.10H2O
  3. filtrationThe solids were filtered out
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 80 mg (43%) of (5-methyl-2-phenyl-4-(trifluoromethyl)thiophen-3-yl)methanol as light yellow oil

Sources & evidence

ORD record
ord-2fec5947aab24353a59269d01b4d37c9
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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