2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethan-1-ol → 2-(2,2-Dimethyl-1,3-dioxolan-4-yl)acetaldehyde

HRID 491400Notes

Reaction equation

HRID 491400 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][CH:5]([CH2:7][CH2:8][OH:9])[CH2:4][O:3]1>ClCCl>[CH3:1][C:2]1([CH3:10])[O:6][CH:5]([CH2:7][CH:8]=[O:9])[CH2:4][O:3]1

Participants

3

Reactant 1

HCID 42197542-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethan-1-ol

Product 1

HCID 109863582-(2,2-Dimethyl-1,3-dioxolan-4-yl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol (530 mg, ALD) in dichloromethane (50 ml) was added with Dess-Martin periodinane[1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one] (2.23 g, LANC), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (flash column chromatography, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate ia-03).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (flash column chromatography, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-33b1c33a2c1f4834bb3b3106363b9089
Source dataset
uspto-grants-2009_05
Patent number
US07531533B2

Reaction notes

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