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

HRID 1010518ノート

反応式

HRID 1010518 の反応式
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]

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 23665647Potassium tert-butoxideHCID 72491401HCID 72491401、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-a4de41af06ef4d7f925083e58500ec8d
出典データセット
uspto-grants-2011_07
特許番号
US07977315B2

反応ノート

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