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Sodium Hydroxide → Methyl rac-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylate

HRID 462623
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인쇄 미리보기

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HRID 462623 반응식
C(O[CH:5]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16](OC(=O)C)[CH:15]2[CH:6]1[C:7](=[O:36])[C:8]1[C:9]3([S:35][CH2:34][CH2:33][S:32]3)[CH2:10][CH:11]([C:28]([O:30][CH3:31])=[O:29])[CH2:12][C:13]=1[C:14]2=[O:27])(=O)C.[OH-].[Na+]>CO.O>[O:36]=[C:7]1[C:6]2[C:15](=[CH:16][C:17]3[C:22]([CH:5]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14](=[O:27])[C:13]2[CH2:12][CH:11]([C:28]([O:30][CH3:31])=[O:29])[CH2:10][C:9]3([S:32][CH2:33][CH2:34][S:35]3)[C:8]1=2
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참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 20283276Methyl rac-1',2',3',4',5',5a',6',11',11a',12'-decahydro-6',11'-diacetoxy-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylate

생성물 1

HCID 20283279Methyl rac-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylate수율 73.1%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 962
Water
용매

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온도
20 °C

실험 절차

A mixture of 26.5 mg (0.05 mmol) of methyl rac-1',2',3',4',5',5a',6',11',11a',12'-decahydro-6',11'-diacetoxy-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylate and 5 mg (0.125 mmol) of sodium hydroxide in 2 ml of methanol was stirred at 20° C. for 1.5 hours. The mixture was then diluted with 10 ml of water and extracted with two 10 ml portions of dichloromethane. The combined dichloromethane extracts were washed with 10 ml of water, dried over magnesium sulphate and evaporated to dryness to give 15 mg (73%) of methyl rac-1',2',3',4',5',12'-hexahydro-5',12'-dioxospiro[1,3-dithiolane-2,4'-naphthacene]-2'-carboxylate in the form of a bright yellow solid of melting point 216° C.

후처리

  1. extractionextracted with two 10 ml portions of dichloromethane
  2. washThe combined dichloromethane extracts were washed with 10 ml of water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-e463b840afeb41938fbd74872a3f393e
출처 데이터셋
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04515969

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