Triacetoxyperiodinane → 1-Benzyl-1H-pyrazole-4-carbaldehyde

HRID 1363313Notes

Reaction equation

HRID 1363313 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[N: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>[CH2:1]([N:8]1[CH:12]=[C:11]([CH:13]=[O:14])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 16769828(1-benzyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 64846761-Benzyl-1H-pyrazole-4-carbaldehydeYield 46.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-Benzyl-1H-pyrazol-4-yl)methanol (190 mg, 1.0 mmol) in DCM (8 mL) at rt was treated with Dess-Martin periodinane (670 mg, 1.58 mmol). After 1.5 h, the reaction was quenched with a mixture of saturated solution of sodium thiosulfate and 10% NaHCO3 (1:1) at rt, stirred for 30 min before extraction with DCM (3×30 mL). The combined extracts were washed with a saturated aqueous solution of NaHCO3, brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (Isco CombiFlash) 0-40% EtOAc/heptane provided 1-benzyl-1H-pyrazole-4-carbaldehyde (86 mg, 46%). 1H NMR (400 MHz, CDCl3) δ ppm 5.35 (s, 2H), 7.27-7.30 (m, 2H), 7.36-7.43 (m, 3H), 7.88 (s, 1H), 8.01 (s, 1H), 9.85 (s, 1H); LCMS-MS (ESI+) 186.90 (M+H).

Workup

  1. customthe reaction was quenched with a mixture of saturated solution of sodium thiosulfate and 10% NaHCO3 (1:1) at rt
  2. washThe combined extracts were washed with a saturated aqueous solution of NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (Isco CombiFlash) 0-40% EtOAc/heptane

Sources & evidence

ORD record
ord-4fdd025cd2d24b9badecf13d64db2436
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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