Triacetoxyperiodinane → (2S)-2-Methyl-5-(phenylmethoxy)pentanal

HRID 1367666Notes

Reaction equation

HRID 1367666 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][CH2:31][CH2:32][CH2:33][C@H:34]([CH3:37])[CH2:35][OH:36])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[CH2:23]([O:30][CH2:31][CH2:32][CH2:33][C@H:34]([CH3:37])[CH:35]=[O:36])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11593688(S)-5-Benzyloxy-2-methyl-pentan-1-ol

Product 1

HCID 11218003(2S)-2-Methyl-5-(phenylmethoxy)pentanalYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (5.19 g, 12.23 mmol, 1.2 equiv) was added to a solution of 34 (2.1 g) in methylene chloride (20 ml) at 0° C. The mixture was stirred at room temperature for 10 min, filtered through a plug of celite and concentrated. Flash column chromatography (10% EtOAc/hexanes) gave aldehyde 25 (1.7 g, 82%) as a colorless oil: [α]22D=+15.5 (c=0.5, CHCl3); TLC Rf=0.87 (silica gel, 50% EtOAc/hexanes); 1H NMR (400 MHz, CDCl3) δ 9.6 (s, 1H), 7.37-7.26 (m, 5H), 4.5 (s, 2H), 3.51-3.46 (t, 3J=6 Hz, 2H), 2.41-2.32 (m, 1H), 1.87-1.78 (m, 1H), 1.74-1.60 (m, 2H), 1.52-1.42 (m, 1H), 1.115-1.097 (d, 3J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 205.23, 136.678, 128.62, 127.863, 73.187, 70.171, 46.298, 27.397, 13.529; HRMS calcd for C13H18O2+Na+ 229.1204; found 229.1221 [M+Na+].

Workup

  1. filtrationfiltered through a plug of celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-927a8f01407b4d3abfee3a93c8cdc7c7
Source dataset
uspto-grants-2011_02
Patent number
US07893268B2

Reaction notes

Loading…