Hydrochloric Acid → 3-Dodecyl-5-methylisoxazole

HRID 264106ノート

反応式

HRID 264106 の反応式
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:4]=1.[BH4-].[Na+].Cl>CS(C)=O>[CH2:8]([C:5]1[CH:4]=[C:3]([CH3:2])[O:7][N:6]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 105443765-(Bromomethyl)-3-dodecylisoxazole

生成物 1

HCID 104913863-Dodecyl-5-methylisoxazole

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A suspension of 5-(bromomethyl)-3-dodecylisoxazole (9.99 g, 0.0302 mol) in dimethylsulfoxide (100 mL) was warmed to give a cloudy solution and allowed to cool. When the temperature reached +35° C., sodium borohydride (1.2 g, 0.032 mol) was added in one portion, and the mixture was stirred for 3 days under nitrogen at room temperature. The mixture was poured into 0.1M HCl (900 mL) and extracted with ether. The organic layer was washed (saturated NaCl), dried (MgSO4), and rotoevaporated. The residue was chromatographed on silica gel (160 g, 70-230 mesh) using petroleum ether-acetone (29:1, 10×200 mL) as eluent. Fraction 6 was rotoevaporated and dried in vacuo to give a white solid; yield 3.96 g (52%); mp 35°-38° C.

後処理

  1. temperaturewas warmed
  2. customto give a cloudy solution
  3. temperatureto cool
  4. customreached +35° C.
  5. extractionextracted with ether
  6. washThe organic layer was washed (saturated NaCl)
  7. dry with materialdried (MgSO4)
  8. customThe residue was chromatographed on silica gel (160 g, 70-230 mesh)
  9. customdried in vacuo
  10. customto give a white solid

出典と根拠

ORDレコード
ord-8771b1b62d9f40e3834d67fd7aad81cb
出典データセット
uspto-grants-1997_07
特許番号
US05646170

反応ノート

読み込み中…