Water → 2-[4-(4-{[tert-Butyl(dimethyl)silyl]oxy}butyl)phenyl]ethan-1-ol

HRID 1479271Notes

Reaction equation

HRID 1479271 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](O)=[O:21])=[CH:15][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[OH:21][CH2:20][CH2:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 596786834-(4-Tert-butyldimethylsilyloxybutyl)phenylacetic acid

Product 1

HCID 596787122-[4-(4-{[tert-Butyl(dimethyl)silyl]oxy}butyl)phenyl]ethan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4-(4-tert-butyldimethylsilyloxybutyl)phenylacetic acid (0.25 g, 0.775 mmol) dissolved in dry ether is added dropwise to a suspension of lithium aluminum hydride in ether (44.2 mg, 1.16 mmol). The reaction mixture is stirred for 5 hours after which water (45 μl), NaOH (15% solution, 45 μl) and water (135 μl) are successively added and the reaction mixture is stirred for a further 30 minutes. The resulting precipitate is filtered

Workup

  1. additionare successively added
  2. filtrationThe resulting precipitate is filtered

Sources & evidence

ORD record
ord-64bab022b4d349078be66a67df200d86
Source dataset
uspto-grants-2016_08
Patent number
US09408927B2

Reaction notes

Loading…