Sodium Bicarbonate → 3a-Methyl-5,6-epoxy-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

HRID 2358278ノート

反応式

HRID 2358278 の反応式
[CH3:1][C:2]12[C:23](=[O:24])[CH2:22][CH2:21][CH:3]1[CH:4]1[C:9]([CH2:10][CH2:11]2)=[C:8]([CH2:12][CH2:13][C:14]2([CH3:19])[O:18][CH2:17][CH2:16][O:15]2)[C:7](=[O:20])[CH2:6][O:5]1.C(=O)(O)[O-:26].[Na+]>ClCCl>[CH3:1][C:2]12[C:23](=[O:24])[CH2:22][CH2:21][CH:3]1[CH:4]1[CH:9]3[CH:10]([O:26][C:8]3([CH2:12][CH2:13][C:14]3([CH3:19])[O:15][CH2:16][CH2:17][O:18]3)[C:7](=[O:20])[CH2:6][O:5]1)[CH2:11]2

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 684591043a-Methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

生成物 1

HCID 684573743a-Methyl-5,6-epoxy-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-30 °C

実験手順

A solution of 70% meta-perobenzoic acid (939 mg, 3.8 mmol) in dichloromethane (20 mL) was added dropwise to a suspension of 3a-methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione (800 mg, 2.53 mmol) and sodium bicarbonate (213 mg, 3.8 mmol) in dichloromethane (51 mL) at −30° C. The resulting mixture was stirred at −30° C. for 16 h. The reaction was then quenched with saturated solution of sodium thiosulfate. The resulting mixture was treated with saturated sodium carbonate solution and then extracted with dichloromethane (2×50 mL). The combined organic layer was dried with magnesium sulfate. The resulting solution was filtered and concentrated to yield the title compound as a white foam.

後処理

  1. customThe reaction was then quenched with saturated solution of sodium thiosulfate
  2. additionThe resulting mixture was treated with saturated sodium carbonate solution
  3. extractionextracted with dichloromethane (2×50 mL)
  4. dry with materialThe combined organic layer was dried with magnesium sulfate
  5. filtrationThe resulting solution was filtered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-b3dfd468cd5d4409b9566c3dc1c77e5c
出典データセット
uspto-grants-2010_07
特許番号
US07763648B2

反応ノート

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