반응 #7154

ord-c9a05f2f40394d91bbdcb528d65562fd

반응 방정식

COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1O
N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide
BrCCBr
1,2-dibromethane
[K+].[OH-]
potassium hydroxide
CCCC[N+](CCCC)(CCCC)CCCC.[OH-]
tetrabutylammonium hydroxide
COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCBr
desired compound
COc1cc(CC(=O)Nc2cccc(C3CCC(C(C)(C)C)CC3)c2)ccc1OCCBr
4-(2-bromoethoxy)-N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-3-methoxyphenylacetamide

반응 조건

온도
50°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    세척The reaction solution is washed with water
  2. 2
    건조the organic layer is dried over sodium sulfate
  3. 3
    기타the solvent is evaporated under reduced pressure
  4. 4
    기타The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

실험 절차

A mixture of N-[3-(4-tert-butylcyclohexan-1-yl)phenyl]-4-hydroxy-3-methoxyphenylacetamide (the compound of Example 20) (1.5 g), 1,2-dibromethane (15 ml), 40% aqueous potassium hydroxide solution (5 ml) and 40% aqueous tetrabutylammonium hydroxide solution (0.5 ml) is stirred at 50° C. for 18 hours. The reaction solution is washed with water, and the organic layer is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (1.6 g).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07084176B2uspto-grants-2006_08