Tributylphosphine → 1-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-ethanone

HRID 2261751ノート

反応式

HRID 2261751 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[N:20]1[C:24]([CH2:25]O)=[C:23]([CH:27]([CH3:29])[CH3:28])[CH:22]=[N:21]1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[N:20]1[C:24]([CH2:25][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=2)=[C:23]([CH:27]([CH3:29])[CH3:28])[CH:22]=[N:21]1

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 701334-Hydroxy-2-methylacetophenoneHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57443256(1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol

生成物 1

HCID 574432701-{4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenyl}-ethanone収率 64%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a 0° C. suspension of 4′-Hydroxy-2′-methylacetophenone (716 mg, 4.77 mmol), [2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-yl]-methanol (1.36 g, 4.77 mmol), tri-n-butylphosphine (1.78 mL, 7.15 mmol) in toluene (20 mL) is added ADDP (1.80 g, 7.15 mmol). The reaction is warmed to room temperature and is stirred overnight. The reaction is concentrated under reduced pressure and the residue is chromatographed (0% to 30% EtOAc/Hex) to yield the title compound (857 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 7.70 (s, 1H), 7.65 (d, 1H, J=8.8 Hz), 7.42-7.38 (m, 2H), 7.32-7.27 (m, 1H), 6.64-6.58 (m, 2H), 4.85 (s, 2H), 2.99 (sept, 1H, J=7.0 Hz), 2.50 (s, 3H), 2.49 (s, 3H), 1.30 (d, 6H, J=7.0 Hz).

後処理

  1. concentrationThe reaction is concentrated under reduced pressure
  2. customthe residue is chromatographed (0% to 30% EtOAc/Hex)

出典と根拠

ORDレコード
ord-4c1aaefa286847ff8d685d77719baf90
出典データセット
uspto-grants-2010_12
特許番号
US07846960B2

反応ノート

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