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

HRID 566508Notes

Reaction equation

HRID 566508 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH:23]([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])=[CH:19][CH:18]=2)([C:12](OC)=[O:13])[C:8](OC)=[O:9])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH:23]([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])=[CH:21][CH:22]=2)([CH2:12][OH:13])[CH2:8][OH:9])=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21265763Dimethyl 2-(4-bromobenzyl)-2-[4-(diethoxymethyl)benzyl]malonate

Product 1

HCID 212657092-(4-Bromobenzyl)-2-[4-(diethoxymethyl)benzyl]-1,3-propanediol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution Dimethyl 2-(4-bromobenzyl)-2-[4-(diethoxymethyl) benzyl]malonate(crude from Step 2) in 200 mL of THF cooled at 0° C. was added of LiAlH4 (0.8 g). The mixture was stirred for 2 h at room temperature and the quenched with acetone (5 mL), followed by 100 mL of 20% aqueous sodium potassium tartrate solution. The mixture was extracted with 200 ML of 2:1 hexane/EtOAc. The extract was dried over Na2SO4 and concentrated to give the crude product which was purified by silica gel chromatography eluted with 2:1 hexane EtOAc containing 1% of Et3N to give 4.2 g of the title compound.

Workup

  1. customthe quenched with acetone (5 mL)
  2. extractionThe mixture was extracted with 200 ML of 2:1 hexane/EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas purified by silica gel chromatography
  7. washeluted with 2:1 hexane EtOAc containing 1% of Et3N

Sources & evidence

ORD record
ord-500d7b05159f414ca63e9550163076fe
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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