Trimethylsilyl triflate → HCID 66992487, compound

HRID 556727Notes

Reaction equation

HRID 556727 reaction equation
[C:1]([O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[OH:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.ClC(Cl)(Cl)C(=N)O[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH3:44])[CH:36]=1>C(Cl)Cl>[C:1]([O:9][C@@H:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[O:16][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH3:44])[CH:36]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 4687839HCID 4687839, compoundHCID 167438072-(3,4-Dimethoxyphenyl)ethyl 2,2,2-trichloroethanimidate

Product 1

HCID 66992487HCID 66992487, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 250 mL round bottom flask equipped with an argon inlet and magnetic stir bar was charged with 2-hydroxycyclohexyl benzoate (7.39 g, 33.6 mmol) in anhydrous CH2Cl2 (50 mL). The solution was cooled to 0° C. prior to the successive addition of trimethylsilyl trifluoromethanesulfonate (3.0 mL, 1.9.4 mmol) and 3,4-dimethoxyphenethyl 2,2,2-trichloroacetimidate (16.5 g, 50.4 mmol) dissolved in anhydrous CH2Cl2 (30 mL). The reaction mixture was stirred at r.t. for 3 days. The reaction was then quenched by the addition of H2O (100 mL). The aqueous layer was extracted with CH2Cl2 (3×100 mL). The combined organic extracts were washed successively with brine (2×100 mL) and distilled water (100 mL), dried over anhydrous MgSO4, and concentrated under vacuum. The crude material was purified by flash column chromatography (EtOAc-hexanes, 1:7, v/v,) to afford a yellow oil (8.69 g, 67%). Rf 0.77 (EtOAc-hexanes, 1:2, v/v,); 1H-NMR (300 MHz, CDCl3) δ 1.36 (m, 2H), 1.62 (m, 4H), 1.85-2.03 (m, 2H), 2.75 (t, 2H), 3.53 (m, 1H), 3.62 (m, 1H), 3.72 (m, 2H), 3.79 (s, 6H, OCH3), 6.76 (m, 3H, Ar), 7.38 (m, 2H, Ar), 7.53 (m, 1H, Ar), 8.00 (m, 2H, Ar).

Workup

  1. customA 250 mL round bottom flask equipped with an argon inlet and magnetic stir bar
  2. customThe reaction was then quenched by the addition of H2O (100 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  4. washThe combined organic extracts were washed successively with brine (2×100 mL)
  5. distillationdistilled water (100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated under vacuum
  8. customThe crude material was purified by flash column chromatography (EtOAc-hexanes, 1:7, v/v,)

Sources & evidence

ORD record
ord-ea834d42a68446e19edfdf3f854a1b83
Source dataset
uspto-grants-2011_11
Patent number
US08058304B2

Reaction notes

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