Dimethyl Disulfide → HCID 59463789, compound

HRID 1713345Notes

Reaction equation

HRID 1713345 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH2:7][CH2:6][C:5]2([CH2:13][CH2:14][OH:15])[CH3:12].[Li]CCCC.[CH3:21][S:22]SC>O1CCCC1>[CH3:12][C:5]1([CH2:13][CH2:14][OH:15])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([S:22][CH3:21])[CH:3]=2)[O:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 59463780HCID 59463780, compoundHCID 178418339Butyllithium

Product 1

HCID 59463789HCID 59463789, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled (−78° C.) solution of 1 g (3.7 mmol) of 2-(6-bromo-4-methylchroman-4-yl)ethanol in 10 mL of dry tetrahydrofuran was added 3.25 mL (8 mmol) of a 2.5 M solution of n-BuLi in hexanes. After 10 minutes, 0.66 mL (7.4 mmol) of dimethyldisulfide was added and the reaction was warmed to room temperature. After 30 minutes, the reaction was cooled to −78° C., quenched with saturated aqueous ammonium chloride, warmed to room temperature and extracted with ethyl acetate. The combined organic fractions were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography eluting with ethyl acetate-hexanes (0-30% gradient) to afford 0.43 g (50%) of 2-(4-methyl-6-methylsulfanylchroman-4-yl)ethanol as an oil.

Workup

  1. waitAfter 30 minutes
  2. temperaturethe reaction was cooled to −78° C.
  3. customquenched with saturated aqueous ammonium chloride
  4. temperaturewarmed to room temperature
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic fractions were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash silica gel chromatography
  10. washeluting with ethyl acetate-hexanes (0-30% gradient)

Sources & evidence

ORD record
ord-1c3ca668b93d49e68a23b811a467f183
Source dataset
uspto-grants-2010_09
Patent number
US07795272B2

Reaction notes

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