Silver Nitrate → 4-(Nitrooxy)butanoic acid

HRID 1374691노트

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HRID 1374691 반응식
CC(C1C=C(SC(SC2C=C(C(C)(C)C)C([O:31][C:32](=[O:37])[CH2:33][CH2:34][CH2:35]Br)=C(C(C)(C)C)C=2)(C)C)C=C(C(C)(C)C)C=1O)(C)C.[N+:42]([O-:45])([O-:44])=[O:43].[Ag+]>C(#N)C.C1COCC1>[N+:42]([O:45][CH2:35][CH2:34][CH2:33][C:32]([OH:31])=[O:37])([O-:44])=[O:43]

참가 물질

4

반응물 2

HCID 24470Silver NitrateHCID 866067714-Bromobutanoic acid [4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl]ester

생성물 1

HCID 98340014-(Nitrooxy)butanoic acid

시약·촉매·용매 1

HCID 22177404Acetonitrile tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of 4-bromobutanoic acid [4-[[1-[[3, 5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenyl]ester (150 mg, 0.22 mmol) in acetonitrile/THF (15 ml 2/1 v/v), AgNO3 was added (80 mg, 0.47 mmol) and the solution was heated in the dark at 60° C. for 6 hours. The silver salt was then filtered off (AgBr) and the solvent was evaporated at reduced pressure. The product thus obtained was purified by chromatography on silica gel with a mixture of ethyl acetate/hexane as eluent (4/6 v/v) to give 4-nitrooxybutanoic acid, [4-[[1-[[3,5-bis(1,1-dimethyletihyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis (1,1-dimethylethyl)-phenyl] ester (100 mg).

후처리

  1. filtrationThe silver salt was then filtered off (AgBr)
  2. customthe solvent was evaporated at reduced pressure
  3. customThe product thus obtained
  4. customwas purified by chromatography on silica gel with a mixture of ethyl acetate/hexane as eluent (4/6 v/v)

출처 및 근거

ORD 기록
ord-453ab883dde1411e8d154dfa0b604362
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166605B2

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