3-(2-Trimethylsilyl-4-furyl)propan-1-ol → 3-(2-Trimethylsilyl-4-furyl)propan-1-al

HRID 1109880Notes

Reaction equation

HRID 1109880 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][Si:13]([CH3:24])([CH3:23])[C:14]1[O:15][CH:16]=[C:17]([CH2:19][CH2:20][CH2:21][OH:22])[CH:18]=1>C(Cl)Cl>[CH3:24][Si:13]([CH3:12])([CH3:23])[C:14]1[O:15][CH:16]=[C:17]([CH2:19][CH2:20][CH:21]=[O:22])[CH:18]=1

Participants

4

Reactant 2

HCID 150370913-(2-Trimethylsilyl-4-furyl)propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 150370923-(2-Trimethylsilyl-4-furyl)propan-1-al

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring mixture of pyridinium chlorochromate (3.89 g, 18.03 mmol) suspended in methylene chloride (100 ml) at 0 degrees was added 3-(2-trimethylsilyl-4-furyl)propan-1-ol (1.19 g, 6.01 mmol), prepared as in Example 2, in dry methylene chloride (15 ml). This mixture was allowed to warm to room temperature, stirred for 90 minutes, filtered and concentrated to give the desired aldehyde.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-769b83a5913440db95476493a8c24ede
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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