Water → Boma

HRID 7725

反応式

HRID 7725 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][C:4]=1[O:18][CH3:19].O.[C-:21]#[N:22].[Na+]>CN(C)C=O>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:21]#[N:22])=[C:4]([O:18][CH3:19])[CH:5]=1

参加物

5

反応物 3

HCID 962WaterHCID 8929Sodium CyanideHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

生成物 1

HCID 10192854Boma

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A mixture of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (318 mg, 1 mmol), dimethylformamide (7.5 mL) and deionzed water (2.5 mL) was stirred at rt. Sodium cyanide (150 mg, 3.0 mmol) was added to reaction. After 3 h, dimethylformamide (10 mL) was added to help dissolve solids in reaction mixture. Let reaction mixture stir overnight at rt. Workup was done by washing reaction with brine (3×30 mL), extraction with EtOAc, combined organic extracts, dried (Na2SO4), filtered and removed solvent in vacuo. Flash chromatography of resulting orange solid on silica gel using a gradient elution of 1:9 EtOAc:hexanes to 1:3 EtOAc:hexanes afforded the desired intermediate, [4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]acetonitrile as a yellow solid. 1H NMR(CDCl3, 300 MHz) δ 7.86–7.36 (m, 7H), 3.99 (s, 3H), 3.74 (s, 2H), 2.59–1.91 (m, 8H). MS (ESI) 265 (M+H)+.

後処理

  1. dissolutionto help dissolve solids
  2. customin reaction mixture
  3. customreaction mixture
  4. stirringstir overnight at rt
  5. washby washing
  6. customreaction
  7. extractionwith brine (3×30 mL), extraction with EtOAc
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customremoved solvent in vacuo
  11. customFlash chromatography of resulting orange solid on silica gel using
  12. washa gradient elution of 1:9 EtOAc

出典と根拠

ORDレコード
ord-8e21f0f9208d4b068d738415af301ac5
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

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