Tetrahydrofuran → 2-methyl-4-[(2-methyl-1-oxo-2,3-dihydro-1H-inden-4-yl)sulfanyl]-1-indanone

HRID 2357867Notes

Reaction equation

HRID 2357867 reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[S:11]C1C=CC=C2C=1CC(C)=C2.Br[C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH2:25][CH:26]([CH3:33])[C:27]2=[O:32].[Li]CCCC.S(Cl)Cl.C1C[O:45]CC1>Cl.CO>[CH3:33][CH:26]1[CH2:25][C:24]2[C:28](=[CH:29][CH:30]=[CH:31][C:23]=2[S:11][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH2:3][CH:2]([CH3:1])[C:10]3=[O:45])[C:27]1=[O:32]

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 25353Sulfur dichlorideHCID 105371524-Bromo-2-methyl-1-indanoneHCID 58897787bis(2-methyl-1H-inden-7-yl)sulfideHCID 178418339Butyllithium

Product 1

HCID 588977942-methyl-4-[(2-methyl-1-oxo-2,3-dihydro-1H-inden-4-yl)sulfanyl]-1-indanone

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Under an argon atmosphere, following the procedure described for bis(2-methyl-1H-inden-7-yl)sulfide, 22.9 g (85.2 mmol) of the above-described dioxalane-protected 4-bromo-2-methylindanone in 150 ml of THF, 34.1 ml of 2.5 M (85.3 mmol) nBuLi in hexanes, and 4.39 g (42.6 mmol) of SCl2 in 35 ml of hexanes gave crude dioxalane-protected 2-methyl-4-[(2-methyl-1-oxo-2,3-dihydro-1H-inden-4-yl)sulfanyl]-1-indanone, which was deprotected in a mixture of 150 ml of 16 M HCl and 150 ml of methanol for 7 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 35 mm, l 400 mm, eluant: CH2Cl2) and then recrystallized from hexanes. Yield, 3.53 g (26%) of a white solid.

Workup

  1. customgave crude dioxalane-protected 2-methyl-4-[(2-methyl-1-oxo-2,3-dihydro-1H-inden-4-yl)sulfanyl]-1-indanone, which
  2. temperatureat reflux
  3. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 35 mm, l 400 mm, eluant: CH2Cl2)
  4. customrecrystallized from hexanes
  5. customYield

Sources & evidence

ORD record
ord-eab22546fb0d44e29196b5f331610b3f
Source dataset
uspto-grants-2010_07
Patent number
US07763562B2

Reaction notes

Loading…