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

HRID 1751878Notes

Reaction equation

HRID 1751878 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 and washed with ether. The ether filtrate is then washed with water and dried. After concentrating the ether, the product obtained is purified by flash chromatography (silica gel; ethyl acetate/hexanes)

Workup

  1. additionare successively added
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with ether
  4. washThe ether filtrate is then washed with water
  5. customdried
  6. concentrationAfter concentrating the ether
  7. customthe product obtained
  8. customis purified by flash chromatography (silica gel; ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-92fbe7b02c6e471d951b47fabbd5797a
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

Loading…