Triacetoxyperiodinane → HCID 63411638, compound

HRID 898201Notes

Reaction equation

HRID 898201 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([OH:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:25]=1>>[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH:25]=1

Participants

3

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 62608744HCID 62608744, compound

Product 1

HCID 63411638HCID 63411638, compoundYield 78.2%

Procedure

Dess-Martin periodinane (4.40 g, 15% solution in methylene chloride, 1.56 mmol) was added to a solution of 1-bromo-3-(1-hydroxyhept-1-yl)benzene (0.39 g, 1.42 mmol, from Aldehyde 75, Step A). After 1 h, the reaction was quenched by the addition of 1N sodium hydroxide (20 mL). The aqueous layer was separated, washed with methylene chloride (20 mL) and the organic layers combined, dried over magnesium sulfate and concentrated in vacuo. Silica gel chromatography eluting with 5% ethyl acetate/hexane gave 0.30 g (1.11 mmol, 78%) of product: 1H NMR (500 MHz) δ 8.08 (t, J=1.7 Hz, 1H), 7.87 (d, J=7.7 Hz, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.34 (t, J=7.9 Hz, 1H), 2.93 (t, J=7.4 Hz, 2H), 1.68-1.76 (m, 2H), 1.28-1.40 (m, 6H), 0.89 (t, J=7.0 Hz, 3H).

Workup

  1. customthe reaction was quenched by the addition of 1N sodium hydroxide (20 mL)
  2. customThe aqueous layer was separated
  3. washwashed with methylene chloride (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. washSilica gel chromatography eluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-833e6356689544558656ddfb7b0f5994
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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