Methanol → Dimethyl 1,3-adamantanedicarboxylate

HRID 992162노트

반응식

HRID 992162 반응식
S(Cl)(Cl)=O.[CH2:5](N(CC)CC)C.[CH3:12][OH:13].[C:14]([C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][C:19]([C:27](O)=[O:28])([CH2:20]3)[CH2:18]1)[CH2:24]2)([OH:16])=[O:15]>CN(C=O)C>[CH3:12][O:13][C:27]([C:19]12[CH2:20][CH:21]3[CH2:22][CH:23]([CH2:24][C:17]([C:14]([O:16][CH3:5])=[O:15])([CH2:26]3)[CH2:18]1)[CH2:25]2)=[O:28]

참가 물질

6

반응물 4

HCID 887MethanolHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 643391,3-Adamantanedicarboxylic acid

생성물 1

HCID 365223Dimethyl 1,3-adamantanedicarboxylate수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In an atmosphere of nitrogen, 10 mmole of 1,3-dicarboxyadamantane obtained by the method of Example 64 was dissolved in 10 ml of DMF. To the mixture, 30 mmole of thionyl chloride was added dropwise over 30 minutes and the mixture was heated to begin to reflux around the conclusion of addition. After refluxing for 2 hours, the mixture was cooled. To the mixture, 40 mmole of triethylamine was added followed by 22 mmole of methanol over 30 minutes while retaining the temperature of the mixture at 10° C. or less, and then stirred for more 2 hours. As a result, the conversion of 1, 3-dicarboxyadamantane was 99%, and 1,3-bis(methoxycarbonyl)adamantane (yield 95%) was formed.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux around the conclusion of addition
  3. temperatureAfter refluxing for 2 hours
  4. temperaturethe mixture was cooled
  5. customat 10° C. or less

출처 및 근거

ORD 기록
ord-1f35c0cca70f468797b4d178f76c3b51
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06468487B1

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