Iodine → Methyl 4-(1-hydroxyindan-1-yl)-crotonate

HRID 2393483Notes

Reaction equation

HRID 2393483 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 22012252Methyl 4-(1-hydroxyindan-1-yl)-crotonateYield 44.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-f7aaf803df1943f3a64779415a8ab21b
Source dataset
uspto-grants-1998_09
Patent number
US05807871

Reaction notes

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