Ethyl formate → HCID 86604612、化合物

HRID 2102226ノート

反応式

HRID 2102226 の反応式
[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

参加物

5

反応物 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 49762843HCID 49762843、化合物

生成物 1

HCID 86604612HCID 86604612、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1e06a640488e4d2f91e25a3eff8208c0
出典データセット
uspto-grants-2009_08
特許番号
US07572922B2

反応ノート

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