Iodine → HCID 22012252、化合物

HRID 378556

反応式

HRID 378556 の反応式
II.[C:3]1(=[O:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.Br[CH2:14]/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18].[Cl-].[NH4+]>O1CCCC1.[Zn]>[OH:12][C:3]1([CH2:14]/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

参加物

7

反応物 4

HCID 807IodineHCID 67351-IndanoneHCID 25517Ammonium ChlorideHCID 53691752-Butenoic acid, 4-bromo-, methyl ester

生成物 1

HCID 22012252HCID 22012252、化合物収率 44.4%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A suspension of activated zinc (80 g) in dry tetrahydrofuran (200 ml) was heated to reflux and a few crystals of iodine was added. A solution of 1-indanone (100 g) and methyl 4-bromo-crotonate (200 g) in 500 ml of dry tetrahydrofuran was added dropwise followed by reflux for 1 h. After cooling, ice and aq. ammonium chloride was added followed by extraction with dichloromethane. Removal of the solvent in vacuo gave a viscous oil which was purified on a silica gel column (eluent: dichloromethane/ether=1:1) giving methyl 4-(1 -hydroxyindan-1-yl)-crotonate (78 g).

後処理

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureby reflux for 1 h
  4. temperatureAfter cooling
  5. extractionfollowed by extraction with dichloromethane
  6. customRemoval of the solvent in vacuo
  7. customgave a viscous oil which
  8. customwas purified on a silica gel column (eluent: dichloromethane/ether=1:1)

出典と根拠

ORDレコード
ord-ae00918947de490e84718b939839e718
出典データセット
uspto-grants-2000_02
特許番号
US06031099

関連ノート

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