Sulfuric Acid → HCID 72491401, 화합물

HRID 1010517노트

반응식

HRID 1010517 반응식
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][CH:9]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[CH2:10][CH:11]([OH:17])[CH:12]([N+:14]([O-:16])=[O:15])[CH3:13].OS(O)(=O)=O>CCOCC.O>[C:1]([O:17][CH:11]([CH2:10][CH:9]([CH3:8])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:26])[CH3:27])[CH:12]([N+:14]([O-:16])=[O:15])[CH3:13])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 72491400HCID 72491400, 화합물

생성물 1

HCID 72491401HCID 72491401, 화합물수율 39.6%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
-10 °C

실험 절차

A flask containing 1.15 g of acetic anhydride was cooled to −10° C. with a salt-ice bath, and 3.1 g of 4 was added with magnetic stirring under an N2 atmosphere. After 10-15 min, 25 mL of concentrated H2SO4 was added. The reaction mixture was allowed to stir for an additional 10 min, after which it was diluted with 40 mL of ether and 10 mL of H2O. The mixture was extracted three times with 15 mL of saturated aqueous sodium bicarbonate and once with 10 mL of saturated aqueous NaCl. The ether layer was dried over anhydrous MgSO4, and the solvent was removed by rotary evaporation to yield 1.40 g of a mixture of stereoisomers of the nitro acetate 5. 1H NMR δ (ppm) 5.4 (br m, CHOCOCH3), 5.2 (t, CH3C(CH3)═CH and CH2C(CH3)═CH), 4.4 (m, CHNO2), 2.1 (s, CH3CO2), 2.0 (m, C═CHCH2CH2C(CH3)═CHCH2), 1.6-1.7 (all s, CH3C(CH3)═CHCH2CH2CCH3), 1.5 (d, CH3CHNO2), 1.2-1.5 (m, CH2CH(CH3)CH2), 0.9 (d, CH2CH(CH3)CH2).

후처리

  1. stirringto stir for an additional 10 min
  2. extractionThe mixture was extracted three times with 15 mL of saturated aqueous sodium bicarbonate
  3. dry with materialThe ether layer was dried over anhydrous MgSO4
  4. customthe solvent was removed by rotary evaporation

출처 및 근거

ORD 기록
ord-bf7d00bf95a94fcda0483354c8fad23d
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977315B2

반응 노트

불러오는 중…