Ethyl formate → HCID 86604612, 화합물

HRID 1669839노트

반응식

HRID 1669839 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 86604612HCID 86604612, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fa94faa07e7145ba86909949c3e7e426
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989475B2

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