Triacetoxyperiodinane → HCID 15864215, compound

HRID 899736Notes

Reaction equation

HRID 899736 reaction equation
[C:1]([N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25][CH2:26][CH2:27][OH:28])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[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>C(Cl)Cl.CCOC(C)=O>[C:1]([N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25][CH2:26][CH:27]=[O:28])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 18422816HCID 18422816, compound

Product 1

HCID 15864215HCID 15864215, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(1-trityl-1H-imidazol-2-yl)-propan-1-ol (201 mg, 0.545 mmol) in CH2Cl2 (6 mL) was added Dess-Martin periodinane (278 mg, 0.655 mmol) at room temperature. After stirring at room temperature for 1 h, the mixture was diluted with EtOAc (30 mL), washed with 1 N NaOH(aq) (2×10 mL) and brine (10 mL), then dried (MgSO4) and concentrated in vacuo to give a tan foam (178 mg, 89%). 1H NMR (CDCl3) δ 2.19 (m, 2H), 2.37 (m, 2H), 6.75 (d, 1H, J=1.5 Hz), 6.93 (d, 1H, J=1.5 Hz), 7.13 (m, 6H), 7.34 (m, 9H), 9.54 (s, 1H).

Workup

  1. washwashed with 1 N NaOH(aq) (2×10 mL) and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ffaace2a84084d40b47087cfef02fd8c
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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