Triacetoxyperiodinane → HCID 24950840, compound

HRID 877397Notes

Reaction equation

HRID 877397 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:17][CH:16]=2)[OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([C:15]2[O:19][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[N:17][CH:16]=2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 583662647-Phenyl-1-(2-(pyridin-2-yl)oxazol-5-yl)-heptan-1-ol

Product 1

HCID 24950840HCID 24950840, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Phenyl-1-(2-(pyridin-2-yl)oxazol-5-yl)-heptan-1-ol (S2, 20 mg, 0.059) was dissolved in CH2Cl2 (4 mL) and Dess-Martin periodinane (1.5 equiv) was added. The mixture was stirred at room temperature for 2 h before silica gel was added and the reaction mixture was evaporated in vacuo to afford the crude ketone absorbed on silica gel. This mixture was subsequently purified by flash chromatography (SiO2, 10-50% EtOAc-hexanes) to yield the title compound (18 mg, 90%) as a white solid: 1H NMR (CDCl3, 500 MHz) δ 8.89 (s, 1H), 8.31 (d, 1H, J=8.0 Hz), 7.99-7.94 (m, 2H), 7.55-7.52 (m, 1H), 7.36-7.33 (m, 2H), 7.26-7.23 (m, 3H), 3.00 (t, 2H, J=7.5 Hz), 2.69 (t, 2H, J=7.5 Hz), 1.87-1.81 (m, 2H), 1.75-1.69 (m, 2H), 1.51-1.47 (m, 4H); 13C NMR (CDCl3, 125 MHz) δ 189.4, 162.6, 150.8, 150.7, 145.6, 143.1, 137.6, 134.7, 128.8, 128.7, 126.2, 126.0, 123.8, 39.7, 36.3, 31.7, 29.4 (2C), 24.1; HRMS-ESI-TOF m/z 335.1750 ([M+H]+, C21H22N2O2 requires 335.1754). 1,3,4-Oxadiazoles (4a-4-d, 8a-8h, 20, 27-30) and 1,2,4-Oxadiazoles (9a-9g, 21-24): General Procedure A.

Workup

  1. additionwas added
  2. customthe reaction mixture was evaporated in vacuo
  3. customto afford the crude ketone
  4. customabsorbed on silica gel
  5. customThis mixture was subsequently purified by flash chromatography (SiO2, 10-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-b71b1977cee94f7492d2187a7ac69038
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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