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

HRID 970280Notes

Reaction equation

HRID 970280 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-33c23296bf64416caeeb89e8bee5073b
Source dataset
uspto-grants-2007_12
Patent number
US07312191B2

Reaction notes

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