Methyl iodide → Chroman

HRID 1985041Notes

Reaction equation

HRID 1985041 reaction equation
CI.[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C1C[O:13][CH2:12][CH2:11]1.C(C1C=CC=CC=1)C>C1COCC1>[O:13]1[C:12]2[C:6](=[CH:7][CH:8]=[CH:9][CH:11]=2)[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 22742125Tetrahydrofuran heptane ethylbenzol

Product 1

HCID 136319Chroman

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 0.9 g (4 mmole) of sulfone ketone in 40 ml of THF is added 2.5 ml (5 mmole, 1.25 eq.) of 2 M of Lithium diisopropylamine(LDA) in heptane/THF/ethylbenzene at −60° C. The mixture is stirred for about 15 minutes, and then 1.24 ml (20 mmole, 5 eq.) of methyl iodide is added. The reaction mixture is stirred for 1 hour at −60° C., and then the cold bath is removed. After stirring overnight, the reaction mixture is partitioned between EtOAc and water, washed with 0.5N HCl, aqueous sodium bicarbonate solution, and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by column chromatography to afford 0.68 g of the desired product as an oil, which solidified upon standing. TLC (30% EtOAc/Hexane, Rf=0.39). Mass spec. m/e=239.1.

Workup

  1. stirringThe reaction mixture is stirred for 1 hour at −60° C.
  2. customthe cold bath is removed
  3. stirringAfter stirring overnight
  4. customthe reaction mixture is partitioned between EtOAc and water
  5. washwashed with 0.5N HCl, aqueous sodium bicarbonate solution, and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-42cfaa4fa5ee4841a63d751c9f6ad5ee
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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