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

HRID 1363313ノート

反応式

HRID 1363313 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 64846761-Benzyl-1H-pyrazole-4-carbaldehyde収率 46.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-4fdd025cd2d24b9badecf13d64db2436
出典データセット
uspto-grants-2011_02
特許番号
US07884124B2

反応ノート

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