Diethyl Ether → (4-(Thiophen-3-yl)phenyl)methanol

HRID 1585864Notes

Reaction equation

HRID 1585864 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:15]=[CH:14][C:9]([C:10](OC)=[O:11])=[CH:8][CH:7]=2)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C>C1COCC1>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:15]=[CH:14][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 4130332Methyl 4-(3-thienyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15186379(4-(Thiophen-3-yl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (4-thien-3-yl)benzoate (552 g, 1.60 mmol) in THF (5 mL) at 0° C. was added 1.0 M lithium aluminum hydride in diethyl ether (1.60 mL, 1.60 mmol) over 10 minutes. The reaction was allowed to stir at ambient temperature for 3 hours, cooled to 0° C., and quenched by dropwise addition of water (0.10 mL), 4 N aq. NaOH (0.10 mL), and water (0.30 mL). The reaction was filtered through a pad of Celite and the filtrate evaporated in vacuo. The title compound was obtained as an oil and was used without furthur purification.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by dropwise addition of water (0.10 mL), 4 N aq. NaOH (0.10 mL), and water (0.30 mL)
  3. filtrationThe reaction was filtered through a pad of Celite
  4. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-d662891269d8474aa9ce15c523ed1f45
Source dataset
uspto-grants-1999_08
Patent number
US05939557

Reaction notes

Loading…