Triacetoxyperiodinane → HCID 59691766, compound

HRID 898198Notes

Reaction equation

HRID 898198 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:34]1[CH:41]=[CH:40][C:37]([CH2:38][OH:39])=[CH:36][C:35]=1[CH3:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(Cl)Cl>[CH3:42][C:35]1[CH:36]=[C:37]([CH:40]=[CH:41][C:34]=1[C:24](=[O:23])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:38]=[O:39]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68811128HCID 68811128, compound

Product 1

HCID 59691766HCID 59691766, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (1.00 g, 2.37 mmol) was added to a solution of 4-(1-hydroxydec-1-yl)-3-methylbenzyl alcohol (0.300 g, 1.07 mmol, from Step B) in methylene chloride (5.0 mL). After 20 min, the reaction was filtered and concentrated in vacuo. Silica gel chromatography eluting with 5% ethyl acetate/hexane gave 0.24 g (0.89 mmol, 83%) of product: 1H NMR (500 MHz) δ 10.0 (s, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.74 (s, 1H), 7.66 (d, J=7.8 Hz, 1H), 2.87 (t, J=7.5 Hz, 2H), 2.51 (s, 3H), 1.66-1.74 (m, 2H), 1.22-1.38 (m, 12H), 0.87 (t, J=7.0 Hz, 3H).

Workup

  1. filtrationthe reaction was filtered
  2. concentrationconcentrated in vacuo
  3. washSilica gel chromatography eluting with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d34d33b321d249eb8fa8cc3329e45d34
Source dataset
uspto-grants-2008_04
Patent number
US07351725B2

Reaction notes

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