Aluminium lithium hydride → 2,2-Di[4-(diethoxymethyl)benzyl]-1,3-propanediol

HRID 566503Notes

Reaction equation

HRID 566503 reaction equation
[CH2:1]([O:3][CH:4]([O:35][CH2:36][CH3:37])[C:5]1[CH:34]=[CH:33][C:8]([CH2:9][C:10]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])=[CH:22][CH:21]=2)([C:15](OC)=[O:16])[C:11](OC)=[O:12])=[CH:7][CH:6]=1)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:36]([O:35][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:34]=[CH:33][C:8]([CH2:9][C:10]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([CH:26]([O:27][CH2:28][CH3:29])[O:30][CH2:31][CH3:32])=[CH:24][CH:25]=2)([CH2:11][OH:12])[CH2:15][OH:16])=[CH:7][CH:6]=1)[CH3:37]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21265732Dimethyl 2,2-di[4-(diethoxymethyl)benzyl]malonate

Product 1

HCID 212657252,2-Di[4-(diethoxymethyl)benzyl]-1,3-propanediol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 2,2-di[4-(diethoxymethyl)benzyl]malonate (3 g, crude) in 200 mL of THF coole at 0° C. was added of LiAlH4 (0.7 g). The mixture was stirred for 0.5 h at room temperature and the quenched with acetone (5 mL), followed by 100 mL of 20% aqeous sodium potassium tartrate solution. The mixture was extracted with 2×200 mL of EtOAc. The extract was dried over Na2SO4 and concentrated to give the crude title compound which was used for next step without further purification.

Workup

  1. customthe quenched with acetone (5 mL)
  2. extractionThe mixture was extracted with 2×200 mL of EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-712c24dee53a4a1ca9c030d3cc98ef83
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

Loading…