Aluminium lithium hydride → 2-(4-Benzyloxy-3,5-dimethoxy-phenyl)-ethanol

HRID 2382561Notes

Reaction equation

HRID 2382561 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:7]([O:21][CH3:22])[CH:6]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:14]([O:13][C:8]1[C:9]([O:11][CH3:12])=[CH:10][C:5]([CH2:4][CH2:3][OH:2])=[CH:6][C:7]=1[O:21][CH3:22])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57436870(4-benzyloxy-3,5-dimethoxy-phenyl)-acetic Acid Methyl Ester

Product 1

HCID 574368712-(4-Benzyloxy-3,5-dimethoxy-phenyl)-ethanolYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Benzyloxy-3,5-dimethoxy-phenyl)-acetic acid methyl ester (3.57 g, 11.3 mmol) was dissolved in THF (113 mL). A solution of LAH (1M in THF, 11.3 mL) was added dropwise to the stirring reaction mixture. After completion of addition the reaction continued to stir at room temperature overnight. The next day, the reaction was quenched with water. The aqueous layer was extracted with ethyl acetate. All of the combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield a crude material (2.89 g, 89%), which was used in the next step without any additional purification.

Workup

  1. additionAfter completion of addition the reaction
  2. customThe next day, the reaction was quenched with water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialAll of the combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3aabc8ff4e664420b89be4f119b507ec
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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