Water → 2,6,10-Trimethyl-13-nitrotetradeca-2,6,12-triene

HRID 970280노트

반응식

HRID 970280 반응식
C(O[CH:5]([CH2:11][CH:12]([CH3:24])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH:6]([N+:8]([O-:10])=[O:9])[CH3:7])(=O)C.CC(C)([O-])C.[K+].CCOCC.O>C(O)(C)(C)C>[CH3:24][CH:12]([CH2:13][CH2:14][CH:15]=[C:16]([CH3:23])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH2:11][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH3:7]

참가 물질

6

반응물 4

HCID 962WaterHCID 3283Diethyl EtherHCID 23665647Potassium tert-butoxideHCID 72491401HCID 72491401, 화합물

생성물 1

HCID 714152562,6,10-Trimethyl-13-nitrotetradeca-2,6,12-triene수율 37.4%

시약·촉매·용매 1

HCID 6386tert-Butanol용매2회

실험 절차

A solution of 1.30 g of 5 in 25 mL of t-butyl alcohol was added to a solution of 30 mL of t-butyl alcohol containing 0.53 g of potassium t-butoxide. The reaction mixture was stirred at room temperature for 1 h, whereupon it was added to 150 mL of ether and 20 mL of H2O. The organic layer was separated and dried over MgSO4, and the solvent was removed by rotary evaporation to afford 0.40 g of racemic RG-4, predominantly the (E)-isomer. 1H NMR δ (ppm) 7.18 (t, CH═CNO2), 5.2 (t, CH3C(CH3)═CH and CH2C(CH3)═CH), 2.19 (s, C═C(CH3)NO2), 2.0 (m, C═CHCH2CH2C(CH3)═CHCH2), 2.2-2.3 (m, CH2C═CNO2), (CH3C═(CH3), 1.6-1.7 (all s, CH3C(CH3)═CHCH2CH2CCH3), 1.2-1.5 (m, CH2CH(CH3)CH2), 0.95 (d, CH2CH(CH3)CH2).

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. customthe solvent was removed by rotary evaporation

출처 및 근거

ORD 기록
ord-33c23296bf64416caeeb89e8bee5073b
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312191B2

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