Methoxytrimethylsilane → HCID 66696670, compound

HRID 1672585Notes

Reaction equation

HRID 1672585 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][CH:12]=[N:11][C:10]=2[CH:14]=[O:15])=[CH:5][CH:4]=1.[CH3:18][O:19][Si](C)(C)C.[CH3:24][Si](OS(C(F)(F)F)(=O)=O)(C)C>C(Cl)Cl>[CH3:24][O:15][CH:14]([O:19][CH3:18])[C:10]1[N:11]=[CH:12][O:13][C:9]=1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 15771MethoxytrimethylsilaneHCID 65367Trimethylsilyl triflateHCID 22473478HCID 22473478, compound

Product 1

HCID 66696670HCID 66696670, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 52B (1.26 g, 5.22 mmol) in CH2Cl2 (5 mL) was cooled to −78° C. after which the starting material was observed to precipitate. Methoxytrimethylsilane (1.44 mL, 10.5 mmol) and trimethylsilyltrifluoromethane sulfonate (0.047 mL, 0.261 mmol) were added and the reaction mixture was allowed to proceed for 24 hr with gradual warming to ambient temperature. The reaction was quenched with saturated aq NaHCO3 solution (10 mL), then diluted with EtOAc (50 mL) and H2O (30 mL). The separated aqueous phase was extracted with EtOAc, and the combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The result was 1.42 g (95%) of the title compound as a yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1H), 7.98 (d, J=8.7, 2H), 7.87 (d, J=8.4, 2H), 5.55 (s, 1H), 3.34 (s, 6H). MS (DCI+) m/z 288 (M+H).

Workup

  1. customto precipitate
  2. customThe reaction was quenched with saturated aq NaHCO3 solution (10 mL)
  3. additiondiluted with EtOAc (50 mL) and H2O (30 mL)
  4. extractionThe separated aqueous phase was extracted with EtOAc
  5. extractionthe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55cf8e54c97d4d7fbed2b5fb89f5e3fb
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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