Triacetoxyperiodinane → 4-(Tert-butyldiphenylsilyloxy)butanal

HRID 1664235Notes

Reaction equation

HRID 1664235 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Si:1]([O:18][CH2:19][CH2:20][CH2:21][CH:22]=[O:23])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 100651081-Butanol, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-

Product 1

HCID 108711124-(Tert-butyldiphenylsilyloxy)butanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the 4-(tert-butyidiphenylsilyloxy)butan-1-ol (0.5 g, 1.5 mmol) in dichloromethane (20 mL) was added Dess-Martin periodinane (775 mg, 1.83 mmol). The mixture was stirred for 1 h. The reaction mixture was poured into hexanes and the resulting white precipitant was removed via filtration. The solution was concentrated to give form a slurry, which was dissolved in dichloromethane (5 mL) and again poured into hexanes resulting in the precipitation of white solid. The solids were removed via filtration and the resulting solution was concentrated. This gave 475 mg (97%) of a clear oil: 1H NMR (CDCl3); δ1.04 (s, 9H), 1.89 (m, 2H), 2.55 (m, 2H), 3.69 (t, 2H, J=6.1 Hz)), 7.38 (m, 6H), 7.63 (d, 4H, J=1.7 Hz), 9.79 (t, 1H, J=1.8 Hz).

Workup

  1. customthe resulting white precipitant was removed via filtration
  2. concentrationThe solution was concentrated
  3. customto give
  4. customform a slurry, which
  5. customThe solids were removed via filtration
  6. concentrationthe resulting solution was concentrated

Sources & evidence

ORD record
ord-cd190b639eb640eeb9528678014f7ccf
Source dataset
uspto-grants-2011_10
Patent number
US08039273B2

Reaction notes

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