Iodine → HCID 22012252, 화합물

HRID 378556

반응식

HRID 378556 반응식
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

참가 물질

7

반응물 4

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

생성물 1

HCID 22012252HCID 22012252, 화합물수율 44.4%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ae00918947de490e84718b939839e718
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06031099

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