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

HRID 2404201노트

반응식

HRID 2404201 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6386tert-Butanol용매HCID 6569Methyl Ethyl Ketone용매

반응 조건

온도
100 °C

실험 절차

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)+.

후처리

  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%

출처 및 근거

ORD 기록
ord-32c93a05a9aa49dabd4bcefff92eb9fc
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802659B2

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