1-Indanone → 1H-Indene-2-acetic acid, 2,3-dihydro-1-oxo-, ethyl ester

HRID 1731147Notes

Reaction equation

HRID 1731147 reaction equation
CCCCCC.C([Li])CCC.[C:12]1(=[O:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CCOCC.[Cl-].[Na+].O.CCCCCC.C1C=CC=CC=1>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][CH:13]1[CH2:14][C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]1=[O:21])[CH3:28]

Participants

8

Reactant 4

HCID 67351-IndanoneHCID 7748Ethyl bromoacetateHCID 8058Hexane2×HCID 178418339Butyllithium

Product 1

HCID 111835591H-Indene-2-acetic acid, 2,3-dihydro-1-oxo-, ethyl ester

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent3×HCID 110624Benzene hexaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A hexane solution containing 0.41 mole of butyllithium is diluted with 1 l. of dry ether. A solution of 1-indanone (50.3 g, 0.38 mole) in 500 ml of dry ether is added dropwise at -10° C with stirring. After the addition is completed, the reaction mixture is stirred for 30 min. A solution of ethyl bromoacetate (63 g) in ether (100 ml) is added slowly from a dropping funnel. The reaction is stopped immediately by careful addition of saturated brine solution. The organic layer is separated and washed several times with fresh portions of the same brine solution. Removal of the ether gives a viscous product which is subjected to chromatography on silica gel using hexane and hexane-benzene (1:1) as eluting solvents. A homogeneous fraction is identified by spectral features. The title compound is more polar than 1-indanone on tlc plate (silica-chloroform), Rf values being 0.65 and 0.55 respectively, νmaxCHCl3 broad peaks at 1765 and 1725 cm-1 , 1640, 1615, 1505 and 1495 cm-1.

Workup

  1. additionis diluted with 1 l
  2. additionAfter the addition
  3. stirringthe reaction mixture is stirred for 30 min
  4. customThe organic layer is separated
  5. washwashed several times with fresh portions of the same brine solution
  6. customRemoval of the ether
  7. customgives a viscous product which
  8. washas eluting solvents

Sources & evidence

ORD record
ord-3451b54e48524e5fa068665f7d0b6961
Source dataset
uspto-grants-1976_11
Patent number
US03995052

Reaction notes

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