Triacetoxyperiodinane → HCID 60026347, compound

HRID 400638Notes

Reaction equation

HRID 400638 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][C:10]=1[C:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][OH:22])[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>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:16])[CH3:17])=[CH:11][C:10]=1[C:19]([CH3:24])([CH3:23])[CH2:20][CH:21]=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 60026622HCID 60026622, compound

Product 1

HCID 60026347HCID 60026347, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-benzyloxy-5-tert-butylphenyl)-3-methylbutan-1-ol (1.7 g, 5.2 mmol) in 20 mL of dichloromethane was added 3.27 g of Dess-Martin periodinane and reaction stirred until TLC indicated the reaction was complete. After 2 hours, the reaction mixture was passed through a pad of silica, eluting with 5% ethyl acetate-hexanes to afford 1.67 g of 3-(2-benzyloxy-5-tert-butylphenyl)-3-methylbutyraldehyde as an oil.

Workup

  1. washeluting with 5% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-8760e4cad4be4afda9fa4e5c03190c43
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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