Triacetoxyperiodinane → HCID 22601320, compound

HRID 970925Notes

Reaction equation

HRID 970925 reaction equation
[Cl:1][C:2]1[CH:20]=[N:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1)=[O:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:20]=[N:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH:15]=[O:16])=[CH:12][CH:13]=1)=[O:5]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22601457HCID 22601457, compound

Product 1

HCID 22601320HCID 22601320, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3,5-Dichloro-N-[4-(2-hydroxy-ethyl)-benzyl]-isonicotinamide (105 mg, 0.32 mmol) in anhydrous CH2Cl2 (2.4 mL) was added Dess-Martin periodinane (206 mg, 0.48 mmol). The resultant solution was stirred at room temperature for 1 h. The mixture was diluted with 100 mL CH2Cl2, filtered through celite, and concentrated in vacuo. The crude product (74 mg, 71%) was used in the next step without further purification.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated in vacuo
  3. customThe crude product (74 mg, 71%) was used in the next step without further purification

Sources & evidence

ORD record
ord-ffdba81b1b5c4ff7a919ce86638af22a
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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