4-(Dimethyl-tert-butylsilyl)oxybutan-1-ol → 4-((Tert-butyldimethylsilyl)oxy)butanal

HRID 1776138Notes

Reaction equation

HRID 1776138 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][OH:24])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)Cl>[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 1864034-(Dimethyl-tert-butylsilyl)oxybutan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 108889764-((Tert-butyldimethylsilyl)oxy)butanalYield 119.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of PCC (161.5 g, 0.75 mol) in DCM (1000 mL) was added 4-(tert-butyl dimethylsilyl oxy)butan-1-ol (102.0 g, 0.5 mol) in 500 mL of DCM, the mixture was stirred for about 1 hr at 0° C., then was warmed to RT and stirred for 2 hours. Then the mixture was filtered and the filtrate was concentrated in vacuo to give the desired compound of 4-(tert-butyldimethylsilyloxy)butanal (5) (121.2 g, yield 60%) as yellow oil which was purified by column chromatography on silica gel (eluent: PE:EA=50:1). 1H NMR (300 MHz, CDCl3): δ 0.04 (S, 6H), 0.0854 (S, 9H), 1.747 (m, 2H), 3.595 (d, J=12 Hz, 1H), 9.677 (d, J=3.3 Hz, 1H); LC-MC found 203 (M+H)+.

Workup

  1. temperaturewas warmed to RT
  2. stirringstirred for 2 hours
  3. filtrationThen the mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5bd318a946af4a7ab256ac2e33bd0ad7
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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