Ethyl 2-(3-methoxyphenyl)-2-methylpropanoate → 2-(3-Methoxyphenyl)-2-methylpropan-1-ol

HRID 716810Notes

Reaction equation

HRID 716810 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:16])([CH3:15])[C:10](OCC)=[O:11])[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:16])([CH3:15])[CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10609062Ethyl 2-(3-methoxyphenyl)-2-methylpropanoate2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 3167872-(3-Methoxyphenyl)-2-methylpropan-1-olYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 2-(3-methoxyphenyl)-2-methyl-propanoate (Intermediate 38, 2 g, 9.0 mmol) in THF (20 mL) at 0° C., lithium aluminium hydride 2M in THF (9.0 ml, 18.0 mmol) was added and the resulting mixture was stirred for 20 minutes at the same temperature. The reaction was quenched with water (10 ml) (slow dropwise addition), and extracted with EtOAc (15 ml). The organic layer was washed with an aqueous 1N solution of HCl (10 ml), dried over Na2SO4 and concentrated in vacuo to afford the title compound (1.439 g) that was used in the next step without further purification.

Workup

  1. customThe reaction was quenched with water (10 ml) (
  2. additionslow dropwise addition), and
  3. extractionextracted with EtOAc (15 ml)
  4. washThe organic layer was washed with an aqueous 1N solution of HCl (10 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cbedf89709d4554b119c9dc148e2291
Source dataset
uspto-grants-2015_11
Patent number
US09193704B2

Reaction notes

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