Diethyl Ether → 5-(alpha-Hydroxyundecyl)-3-phenylbenzofuran

HRID 262217

反応式

HRID 262217 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1.[Mg].[Cl-].[NH4+].C([O:22][CH2:23][CH3:24])C>O1CCCC1.O>[OH:22][CH:23]([C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1)[CH2:24][CH2:4][CH2:3][CH2:2][CH2:16][CH2:6][CH2:7][CH2:10][CH2:11][CH3:12]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 203301645-Bromo-3-phenyl-1-benzofuran

生成物 1

HCID 213202985-(alpha-Hydroxyundecyl)-3-phenylbenzofuran

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5.5 g. (0.02 mole) of 5-bromo-3-phenylbenzofuran in tetrahydrofuran is added 0.5 g. (0.02 mole) of magnesium, and the mixture is heated at its reflux temperature for three hours. After cooling to 0° C., 3.4 g. of undecyl aldehyde is added. After stirring for 30 minutes at room temperature, the solution is added to ammonium chloride solution. Evaporation provides a residue which is mixed with diethyl ether and water. The ether layer is separated, washed with saturated sodium chloride solution, dried and evaporated. The resulting oil is dissolved in carbon tetrachloride and eluted from a silica gel column with carbon tetrachloride, then with dichloromethane. The later fractions are evaporated to provide 5-(α-hydroxyundecyl)-3-phenylbenzofuran which is dissolved in dichloromethane.

後処理

  1. temperaturereflux temperature for three hours
  2. customEvaporation
  3. customprovides a residue which
  4. customThe ether layer is separated
  5. washwashed with saturated sodium chloride solution
  6. customdried
  7. customevaporated
  8. dissolutionThe resulting oil is dissolved in carbon tetrachloride
  9. washeluted from a silica gel column with carbon tetrachloride
  10. customThe later fractions are evaporated

出典と根拠

ORDレコード
ord-c49d250a9e154af5b535095b9dcf3100
出典データセット
uspto-grants-1979_05
特許番号
US04153716

関連ノート

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