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

HRID 1820304노트

반응식

HRID 1820304 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c918402f014e4d6fa8474455522d93bb
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601843B2

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