Hydrogen Peroxide → HCID 58813156、化合物

HRID 601717ノート

反応式

HRID 601717 の反応式
C(N1[C@H:12]([CH3:13])[C@H:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)OC1=O)(=O)CCCCC.[Li+].[OH-:22].[OH:23]O>C1COCC1.O>[CH2:11]([C@H:14]([CH2:15][CH2:16][CH2:17][CH3:18])[C:19]([OH:23])=[O:22])[CH:12]=[CH2:13]

参加物

6

反応物 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 10858719HCID 10858719、化合物

生成物 1

HCID 58813156HCID 58813156、化合物収率 63%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of the compound of step G (2) (1.22 g, 3.86 mmol) in THF (15.6 mL) was added water (3.86 mL), and the mixture cooled to 0° C. A solution of LiOH (185.7 mg, 7.75 mmol) and 30% H2O2 (3.51 mL) in water (12.1 mL) was added, and the combined mixture stirred for 10 minutes at 0° C. The ice bath was removed, and the reaction was allowed to continue for 1 h at rt. A solution of sodium sulfite (440 mg) was added, and the reaction stirred for 10 min. Saturated sodium carbonate solution was added, and the reaction was extracted with methylene chloride. The aqueous layer was acidified to pH 1 with 6 N HCl, and extracted 3 times with diethyl ether. The combined ether layers were washed with brine, and dried over MgSO4. The extract was filtered, and concentrated in vacuo to afforded the desired product (63% yield). 1H NMR (500 MHz, CDCl3) δ ppm 0.88 (t, J=7.0 Hz, 3H) 1.22-1.41 (m, 4H) 1.43-1.57 (m, 1H) 1.57-1.73 (m, 1H) 2.18-2.31 (m, 1H) 2.32-2.53 (m, 2H) 4.97-5.14 (m, 2H) 5.65-5.87 (m, 1H) 9.85 (s, 1H).

後処理

  1. customThe ice bath was removed
  2. waitto continue for 1 h at rt
  3. additionA solution of sodium sulfite (440 mg) was added
  4. stirringthe reaction stirred for 10 min
  5. additionSaturated sodium carbonate solution was added
  6. extractionthe reaction was extracted with methylene chloride
  7. extractionextracted 3 times with diethyl ether
  8. washThe combined ether layers were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationThe extract was filtered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4b91e7eb3ec24653a4e32108240a384e
出典データセット
uspto-grants-2011_03
特許番号
US07902218B2

反応ノート

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