Sodium Hydroxide → Methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylate

HRID 1820304ノート

反応式

HRID 1820304 の反応式
[C:1]12([C:15](OC)=[O:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([C:11]([O:13][CH3:14])=[O:12])([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[OH:16][CH2:15][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([C:11]([O:13][CH3:14])=[O:12])([CH2:4]3)[CH2:2]1)[CH2:8]2

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 365223Dimethyl 1,3-adamantanedicarboxylateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 18410517Methyl 3-hydroxymethyltricyclo[3.3.1.1 3,7]decane-1-carboxylate収率 19%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

After dissolving dimethyl 1,3-adamantanedicarboxylate (1.00 g, 3.96 mmol) in tetrahydrofuran (5 mL), diisobutylaluminum hydride (0.95 M; 5.0 mL, 4.75 mmol) was added dropwise while cooling on ice, and then the mixture was further stirred for 3 hours while cooling on ice. After the reaction, water (0.2 mL) and then aqueous 15% NaOH (0.2 mL) were added dropwise at room temperature, and the mixture was stirred for 30 minutes. Next, water (0.6 mL) and anhydrous magnesium sulfate were added and stirred therewith, and the insoluble portion was filtered out. The solvent was distilled off under reduced pressure, and the obtained residue was subjected to chromatography (50 g Merck Art. 9385, hexane:ethyl acetate=3:2) to obtain the title compound as a colorless oil (0.1648 g, 0.735 mmole) (19% yield).

後処理

  1. additionwas added dropwise
  2. temperaturewhile cooling on ice
  3. temperaturewhile cooling on ice
  4. stirringthe mixture was stirred for 30 minutes
  5. stirringstirred
  6. filtrationthe insoluble portion was filtered out
  7. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-c918402f014e4d6fa8474455522d93bb
出典データセット
uspto-grants-2009_10
特許番号
US07601843B2

反応ノート

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