2,2,2-Trifluoro-N-methoxy-N-methylacetamide → 1-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-2,2,2-trifluoro-ethanone

HRID 713972Notes

Reaction equation

HRID 713972 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH:13]3[CH2:18][CH2:17][CH:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]3)[CH:8]=2)[CH:3]=1.[F:23][C:24]([F:32])([F:31])[C:25](N(OC)C)=[O:26]>C1COCC1>[C:19]([CH:16]1[CH2:15][CH2:14][CH:13]([O:12][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[CH:3]=[C:2]([C:25](=[O:26])[C:24]([F:32])([F:31])[F:23])[CH:11]=[CH:10]3)[CH2:18][CH2:17]1)([CH3:20])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 27823822,2,2-Trifluoro-N-methoxy-N-methylacetamideHCID 509863542-Bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalene

Product 1

HCID 681727961-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-2,2,2-trifluoro-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-Bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalene (2 g, 0.006 mol) in 15 mL dry THF stirring at −78° C., was added dropwise. The reaction was then stirred at −78° C. for 15 minutes, yellow color results. 2,2,2-Trifluoro-N-methoxy-N-methyl-acetamide (1.0 mL, 0.0083 mol) in 10 mL THF was then added dropwise while the reaction was stirred at −78° C. Once all of the starting material was added reaction the reaction was allowed to warm to room temperature while stirring for 2 hours. The Reaction was then quenched with water and extracted three times with EtOAc. Organics were dried over MgSO4, filtered, and concentrated to dryness under reduced pressure. Crude NMR shows about 80% purity (looks like des-bromostarting material). Material was purified via column chromatography using a gradient of hexanes for one column volume followed by 0-10% EtOAC/Hexanes on 25 g of SiO2 to give the title compound as a yellow solid. Material will be carried on without additional purification

Workup

  1. customyellow color results
  2. stirringwas stirred at −78° C
  3. additionOnce all of the starting material was added
  4. customreaction the reaction
  5. temperatureto warm to room temperature
  6. stirringwhile stirring for 2 hours
  7. customThe Reaction was then quenched with water
  8. extractionextracted three times with EtOAc
  9. dry with materialOrganics were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure
  12. customMaterial was purified via column chromatography

Sources & evidence

ORD record
ord-8a44d3772ee74440bc3752d7f67c063c
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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