Methyl iodide → HCID 18546294, compound

HRID 1267487Notes

Reaction equation

HRID 1267487 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]([CH2:36][CH:37]=[CH2:38])[CH:20]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=3)[C:21](=[O:25])[O:22]2)=[CH:17][CH:16]=1.[CH3:39]I>O1CCCC1>[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]([CH2:36][CH:37]=[CH2:38])[C:20]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=3)([CH3:39])[C:21](=[O:25])[O:22]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 18546282HCID 18546282, compound

Product 1

HCID 18546294HCID 18546294, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A 1M solution of lithium hexamethyl-disilazide in tetrahydrofuran (170 ml) was added dropwise to a solution of 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)chroman-2-one (32.70 g) in anhydrous tetrahydrofuran (400 ml) at −73° C. over 15 minutes under nitrogen atmosphere, followed by stirring for 30 minutes at −10° C. The reaction mixture was cooled to −75° C. and methyl iodide (10.6 ml) was added dropwise thereto over 10 minutes, followed by stirring for 10 minutes at −75° C., for 1 hour at −10° C. and then for 1 hour at 0° C. The reaction mixture was quenched with saturated aqueous ammonium chloride and partitioned between ethyl acetate and water. The organic layer was washed twice with water and dried over sodium sulfate. After concentration under reduced pressure, the resulting oil was purified by flash column chromatography (silica gel: Merck Kieselgel 60, eluent: hexane/ethyl acetate=9/1) to give (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-(2-propenyl)chroman-2-one (30.74 g, Yield 90.8%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to −75° C.
  2. waitover 10 minutes
  3. stirringby stirring for 10 minutes at −75° C., for 1 hour at −10° C.
  4. waitfor 1 hour at 0° C
  5. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  6. custompartitioned between ethyl acetate and water
  7. washThe organic layer was washed twice with water
  8. dry with materialdried over sodium sulfate
  9. concentrationAfter concentration under reduced pressure
  10. customthe resulting oil was purified by flash column chromatography (silica gel: Merck Kieselgel 60, eluent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-119833938be648f3a052b47a4aeaab05
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

Loading…