Diethyl Ether → 3-((Tert-butyldimethylsilyl)oxy)propanal

HRID 1708080Notes

Reaction equation

HRID 1708080 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Si:12]([O:19][CH2:20][CH2:21][CH2:22][OH:23])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].CCOCC>ClCCl>[Si:12]([O:19][CH2:20][CH2:21][CH:22]=[O:23])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 36623923-((Tert-butyldimethylsilyl)oxy)propanalYield 55.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of pyridinium chlorochromate (8.50 g, 39.4 mmol) in dichloromethane (53 ml), stirred at room temperature under dry nitrogen, was added 3-(t-butyldimethylsilyloxy)propan-1-ol (5.00 g, 26.3 mmol). After 1.5 hr, dry ether (50 ml) was added and the supernatant liquid decanted from a black gum. The residual gum was washed with ether (3×50 ml) and the combined organic portions passed through a column of Florisil. The resulting brown solution was evaporated then the residue taken up in dichloromethane and passed through fresh Florisil to give a yellow solution from which the solvent was removed to leave a brown liquid (2.75 g). This material was shown by 1Hnmr analysis to be approximately 40% pure and was used without further purification; δH (CDCl3) 0.10 (6H, s, CH3), 0.93 (9H, s, C(CH3)3), 0.63 (2H, dt, J 2 HZ and 6 Hz respectively, CH2), 4.03 (2H, t, J 6 Hz, CH2O ), 9.97 (1H, d, J 2 Hz, CHO).

Workup

  1. customthe supernatant liquid decanted from a black gum
  2. washThe residual gum was washed with ether (3×50 ml)
  3. customThe resulting brown solution was evaporated
  4. customto give a yellow solution from which the solvent
  5. customwas removed

Sources & evidence

ORD record
ord-2bc4131ccc784134b2e719d14ed978ba
Source dataset
uspto-grants-1994_10
Patent number
US05356886

Reaction notes

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