Sodium Iodide → HCID 86703674, compound

HRID 1849792Notes

Reaction equation

HRID 1849792 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C[Si](C)(C)C[C:21](F)([F:23])[F:22].[I-].[Na+]>O1CCCC1>[F:22][C:21]1([F:23])[C:1]2([CH2:7][O:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=3)[CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2]2

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 20398444HCID 20398444, compoundHCID 86703673HCID 86703673, compound

Product 1

HCID 86703674HCID 86703674, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
115 °C

Procedure

To a microwave 5 mL vial was added 1-((cyclohexenylmethoxy)- methyl)-4-methoxybenzene (0.46 g, 2.00 mmol), trimethyl(2,2,2-trifluoroethyl)silane (0.57 g, 4.00 mmol) and sodium iodide (0.66 g, 4.40 mmol) in anhydrous tetrahydrofuran (1.0 mL). The vial was degassed with nitrogen and sealed. The reaction mixture was heated in the microwave reactor at 115° C. for 1 hour. The reaction vial was cooled and the TLC showed presence of starting material. To the reaction vial was added trimethyl(2,2,2-trifluoroethyl)silane (0.5 mL) and continued heating in the microwave at the same temperature for another 1 hour. The reaction was filtered, washed with ethyl acetate (10 ml). The filtrate was concentrated in vacuo to dryness. The residue was purified by column chromatography with ethyl acetate in hexanes (20%) to afford the title compound as colourless liquid (0.45 g, 80%).

Workup

  1. customThe vial was degassed with nitrogen
  2. customsealed
  3. temperatureThe reaction vial was cooled
  4. additionTo the reaction vial was added trimethyl(2,2,2-trifluoroethyl)silane (0.5 mL)
  5. temperaturecontinued heating in the microwave at the same temperature for another 1 hour
  6. filtrationThe reaction was filtered
  7. washwashed with ethyl acetate (10 ml)
  8. concentrationThe filtrate was concentrated in vacuo to dryness
  9. customThe residue was purified by column chromatography with ethyl acetate in hexanes (20%)

Sources & evidence

ORD record
ord-44b045124de94b45a9422cdfc4079d7e
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…