Diethyl Ether → HCID 20591842, 화합물

HRID 1010520노트

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HRID 1010520 반응식
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][CH:9]([CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH2:10][CH:11]([OH:17])[CH:12]([N+:14]([O-:16])=[O:15])[CH3:13].CCOCC>OS(O)(=O)=O.O>[C:1]([O:17][CH:11]([CH2:10][CH:9]([CH3:8])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[CH:12]([N+:14]([O-:16])=[O:15])[CH3:13])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 110642295,9-Dimethyl-2-nitrodec-8-en-3-ol

생성물 1

HCID 20591842HCID 20591842, 화합물수율 88%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 962Water용매

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온도
-10 °C

실험 절차

A flask containing 1.3 g of acetic anhydride was cooled to −10° C. with a salt-ice bath, and 2.34 g of 6 was added with magnetic stirring under an N2 atmosphere. After 10-15 min, 2-5 drops of concentrated H2SO4 were added. The reaction mixture was allowed to stir for an additional 10 min, after which it was treated 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 2.41 g (88%) of a mixture of stereoisomers of the nitro acetate 7. 1H NMR δ (ppm) 5.4 (broad m, CH2CH(OAc)), 5.2 (t, C═CH), 4.65 (m, CH3CHNO2), 2.1 (s, CH3CO2), 2.0 (br m, ═CHCH2), 1.60 and 1.65 (both s, CH3C(CH3)═), 1.5 (d, CH3CHNO2), 1.2-1.5 (m, CH2CH(CH3)CH2), 0.95 (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-2289f45b84124621bf0d394a7ff98d03
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977315B2

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