Ethyl formate → HCID 86604612, compound

HRID 1669839Notes

Reaction equation

HRID 1669839 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[CH:20](OCC)=[O:21]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([C:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH:20]=[O:21])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 49762843HCID 49762843, compound

Product 1

HCID 86604612HCID 86604612, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.84 g 3-(4-bromophenyl)-1-cyclohexylpropan-1-one from Step B above in 50 mL anhydrous THF was added 1.15 g 60% sodium hydride followed by one 6.2 mL and five 3.2 mL portions of ethyl formate over one day. The resulting mixture was stirred at room temperature under nitrogen for another day. The solvent was removed under reduced pressure and the residue was partitioned between cold 0.1 N HCl and ether. The combined ether extract was washed with water (2×), 5% NaHCO3 (3×), water, and saturated brine, dried over anhydrous Na2SO4, and evaporated to give crude product as orange solid. It was purified on silica gel using 10˜15% EtOAc in hexanes to give the title compounds as pink oily solid. 1H NMR (CDCl3, 500 MHz) δ 15.43 (d, J=7.1 Hz, 1H), 8.01 (d, J=7.1 Hz, 1H), 7.43˜7.45 (m, 2H), 7.07 (d, J=8.3 Hz, 2H), 3.52 (s, 2H), 2.32 (tt, J=11.5 & Hz, 1H), 1.73˜1.77 (m, 2H), 1.63˜1.68 (m, 1H), 1.49˜1.53 (m, 2H), 1.39˜1.47 (m, 2H), 1.07˜1.25 (m, 4H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between cold 0.1 N HCl and ether
  3. extractionThe combined ether extract
  4. washwas washed with water (2×), 5% NaHCO3 (3×), water, and saturated brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated
  7. customto give crude product as orange solid
  8. customIt was purified on silica gel using 10˜15% EtOAc in hexanes

Sources & evidence

ORD record
ord-fa94faa07e7145ba86909949c3e7e426
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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