Sodium Iodide → HCID 21990868, compound

HRID 7902Notes

Reaction equation

HRID 7902 reaction equation
CS(O[CH2:6][CH2:7][C:8]12[CH2:20][C:19]3[CH:18]=[C:17]([O:21][CH3:22])[CH:16]=[CH:15][C:14]=3[C:13]1=[C:12]([CH3:23])[C:11](=[O:24])[CH2:10][CH2:9]2)(=O)=O.[I-:25].[Na+]>CC(C)=O>[I:25][CH2:6][CH2:7][C:8]12[CH2:9][CH2:10][C:11](=[O:24])[C:12]([CH3:23])=[C:13]1[C:14]1[C:19](=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=1)[CH2:20]2

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 21990870HCID 21990870, compound

Product 1

HCID 21990868HCID 21990868, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 2-(2-methoxy-5-methyl-6-oxo-6,7,8,9-tetrahydro-8aH-fluoren-8a-yl)ethyl methanesulfonate (49.7 mg, 0.142 mmol) in acetone (2.0 mL) was treated with sodium iodide (85 mg, 0.57 mmol) and the resulting mixture was stirred and heated in an oil bath at 60° C. for 16 hours. After cooling, the mixture was diluted with acetone (2 mL) and filtered through a 0.45 Fm Acrodisc filter. The filtrate was evaporated under vacuum and the residue in CH2Cl2 (3 mL) was re-filtered. The filtrate was purified by chromatography on a Biotage Flash 12M KP-Sil column (12 mm×15 cm) which was eluted with 4:1 hexanes-EtOAc, collecting 6 mL fractions every 30 seconds. Fractions 9-11 gave 9a-(2-iodoethyl)-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (34.5 mg, 64% yield) as an oil.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered through a 0.45 Fm Acrodisc
  3. filtrationfilter
  4. customThe filtrate was evaporated under vacuum
  5. filtrationthe residue in CH2Cl2 (3 mL) was re-filtered
  6. customThe filtrate was purified by chromatography on a Biotage Flash 12M KP-Sil column (12 mm×15 cm) which
  7. washwas eluted with 4:1 hexanes-EtOAc
  8. customcollecting 6 mL fractions every 30 seconds

Sources & evidence

ORD record
ord-6ca20c97881a46a7b3a605c4a606073c
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Reaction notes

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