HCID 19774074, compound → HCID 54145545, compound

HRID 1613558Notes

Reaction equation

HRID 1613558 reaction equation
[C:1]([C:4]1([CH2:7][S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:15][Mg]Br>C(OCC)C>[C:9]1([S:8][CH2:7][C:4]2([C:1]([OH:3])([CH3:15])[CH3:2])[CH2:6][CH2:5]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 19774074HCID 19774074, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 54145545HCID 54145545, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred and ice-cooled solution of 6 (6.16 g, 29.9 mmol) in diethyl ether (60 mL) was added a solution of methylmagnesium bromide (3.0M solution in diethyl ether, 12 mL) dropwise over 10 min under nitrogen. The mixture was stirred for 20 min. The reaction was quenched by an addition of ammonium chloride solution and the organic layer was separated. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with brine, and dried over sodium sulfate. Filtration and concentration gave 5.80 g of an oily material, which was purified by column chromatography (silica gel 60 g, 4-10% ethyl acetate in n-hexane) to give 4.83 g (71.2%) of 7, as a colorless oil.

Workup

  1. stirringThe mixture was stirred for 20 min
  2. customThe reaction was quenched by an addition of ammonium chloride solution
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with diethyl ether
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-54dcfc3ce7a449ad8ee792d31992334b
Source dataset
uspto-grants-1993_03
Patent number
US05194431

Reaction notes

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