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Methyl iodide → (+/-)-3-(2,4-Dichloro-phenyl)-7-(1-methoxymethyl-butoxy)-2,6-dimethyl-pyrazolo[5,1-b]oxazole

HRID 1671300
ノート
印刷プレビュー

反応式

HRID 1671300 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([O:19][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:21][OH:22])=[C:11]2[O:12][C:13]=1[CH3:14].[H-].[Na+].[CH3:28]I.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([O:19][CH:20]([CH2:21][O:22][CH3:28])[CH2:23][CH2:24][CH3:25])=[C:11]2[O:12][C:13]=1[CH3:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6328Methyl iodide2 回HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67212550(+/-)-2-[3-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-yloxy]-pentan-1-ol

生成物 1

HCID 59186038(+/-)-3-(2,4-Dichloro-phenyl)-7-(1-methoxymethyl-butoxy)-2,6-dimethyl-pyrazolo[5,1-b]oxazole

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a stirring solution of (±)-2-[3-(2,4-dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-yloxy]-pentan-1-ol (60 mg, 0.157 mmol) in THF (1.565 ml) at RT is added NaH (6.26 mg, 0.157 mmol). After 10 mins MeI (10.77 μl, 0.172 mmol) is added and the reaction mixture is stirred for a further 3 hours. An additional 1.leq of MeI (10.77 μl, 0.172 mmol) is added and reaction continued for 1 hour whereupon it is added to sat. ammonium chloride (50 ml) and the product extracted into EtOAc (60 ml). The organics are washed with brine, dried over MgSO4 and concentrated in vacuo. The crude reaction products are purified by ISCO combiflash chromatography, eluting with 0 to 100% (iso-hexane/EtOAc) on a 12 g SiO2-column to give (±)-3-(2,4-Dichloro-phenyl)-7-(1-methoxymethyl-butoxy)-2,6-dimethyl-pyrazolo[5,1-b]oxazole as a solid; MS: m/z 397.20 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.58 (2H, m), 7.41 (1H, dd), 4.03 (1H, m), 3.58 (2H, m), 3.44 (3H, s), 2.33 (3H, s), 2.30 (3H, s), 1.76 (2H, m), 1.57 (2H, m), 1.00 (3H, t).

後処理

  1. customreaction
  2. waitcontinued for 1 hour whereupon it
  3. extractionthe product extracted into EtOAc (60 ml)
  4. washThe organics are washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude reaction products
  8. customare purified by ISCO combiflash chromatography
  9. washeluting with 0 to 100% (iso-hexane/EtOAc) on a 12 g SiO2-column

出典と根拠

ORDレコード
ord-a27e1914fe674b888828e3c0e9cdefcf
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07994203B2

反応ノート

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