Potassium tert-butoxide → (2-Cyclohexa-1,3-dienyl-ethoxymethyl)-benzene

HRID 1804764Notes

Reaction equation

HRID 1804764 reaction equation
C1(S([C:10]2([CH2:16][CH2:17][O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14][CH2:13][CH:12]=[CH:11]2)(=O)=O)C=CC=CC=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[C:10]1([CH2:16][CH2:17][O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:15][CH2:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59152663[2-(1-Benzenesulfonyl-cyclohex-2-enyl)-ethoxymethyl]-benzene

Product 1

HCID 59152681(2-Cyclohexa-1,3-dienyl-ethoxymethyl)-benzene

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

[2-(1-Benzenesulfonyl-cyclohex-2-enyl)-ethoxymethyl]-benzene (8) (16 g, 44.9 mmol) is dissolved in tert. butanol (450 ml) and after addition of potassium tert.-butoxide (11.1 g, 98.7 mmol) the mixture is stirred for 32 h at 80° C. Then the mixture is poured on ice and extracted with pentane. The organic layer is separated, washed with saturated NaCl-solution and dried over Na2SO4. The crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel).

Workup

  1. additionThen the mixture is poured on ice
  2. extractionextracted with pentane
  3. customThe organic layer is separated
  4. washwashed with saturated NaCl-solution
  5. dry with materialdried over Na2SO4
  6. customThe crude product is purified by Flash-chromatography (ethyl acetate/hexanes (1:9), silicagel)

Sources & evidence

ORD record
ord-e032fb1822074790b8b54fad0eb40f5d
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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