Aluminium lithium hydride → HCID 66959407, compound

HRID 1958861Notes

Reaction equation

HRID 1958861 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([O:14][CH3:15])=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([O:14][CH3:15])=[C:8]([CH2:9][OH:10])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866570083-(2,6-Dimethylbenzyloxy)-2-methoxybenzaldehyde

Product 1

HCID 66959407HCID 66959407, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2,6-Dimethylbenzyloxy)-2-methoxybenzaldehyde (Step B, 10.6 g, 32.7 mmol) in dry THF (40 ml) was added drop wise LiAlH4 (1M in THF, 0.95 g, 23.7 mmol) at 0° C. under argon. The reaction mixture was stirred for 1 hours or until all the starting material is consumed, then quenched by adding water slowly, followed by addition of 1N HCl (5 ml), water (10 ml), and EtOAc (20 ml) was added to the reaction mixture. The reaction mixture was concentrated, and passed through a short silica gel column using ethyl acetate to give the title compound as an off white solid.

Workup

  1. customis consumed
  2. customquenched
  3. additionby adding water slowly
  4. additionfollowed by addition of 1N HCl (5 ml), water (10 ml), and EtOAc (20 ml)
  5. additionwas added to the reaction mixture
  6. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-f117fc55acda429b91553d365c579183
Source dataset
uspto-grants-2013_04
Patent number
US08410154B2

Reaction notes

Loading…