Cesium carbonate → 3-(4-Tert-butyl-cyclohexyloxy)-1-iodo-naphthalene

HRID 713980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 713980
[I:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.[C:13]([CH:17]1[CH2:22][CH2:21][CH:20](OS(C)(=O)=O)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>C(O)(C)(C)C.CC(=O)CC>[C:13]([CH:17]1[CH2:22][CH2:21][CH:20]([O:12][C:4]2[CH:3]=[C:2]([I:1])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 11128255Methanesulfonic acid 4-tert-butyl-cyclohexyl esterHCID 220671024-Iodonaphthalen-2-ol

Produkt 1

HCID 681728013-(4-Tert-butyl-cyclohexyloxy)-1-iodo-naphthaleneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6386tert-ButanolLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-iodo-naphthalen-2-ol (1.0 g, 3.7 mmol) (See, for example. Australian Journal of Chemistry (1963), 16 401-10. b. Journal of the Chemical Society (1943), 468-9, which is incorporated by reference in its entirety), methanesulfonic acid 4-tert-butyl-cyclohexyl ester 1.8 g, 7.4 mmol) and cesium carbonate (3.6 g, 11 mmol) in tert-butyl alcohol (10 mL) and 2-butanone (7 mL) was heated in a sealed vial at 100° C. for 4 hrs. The mixture was partitioned between water and dichloromethane. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified via a silica gel column eluted with EtOAc in hexanes from 0 to 30% to give light yellow precipitate (1.10 g, yield: 73%). ESI-MS: 409.10 (M+H)+.

Aufarbeitung

  1. customThe mixture was partitioned between water and dichloromethane
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via a silica gel column
  7. washeluted with EtOAc in hexanes from 0 to 30%

Quellen und Nachweise

ORD-Eintrag
ord-f32834fdffa240dbb1aa759dd88c6ae4
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09186367B2

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