Cesium carbonate → HCID 178445718, 화합물

HRID 713862노트

반응식

HRID 713862 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[C@H:24]1[CH2:29][CH2:28][C@H:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:26][CH2:25]1)(=O)=O>C(O)(C)(C)C.CC(=O)CC>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][C@H:24]3[CH2:29][CH2:28][C@H:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:26][CH2:25]3)[CH:8]=2)[CH:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 271446-Bromo-2-naphthalenolHCID 178445816HCID 178445816, 화합물

생성물 1

HCID 178445718HCID 178445718, 화합물수율 32%

시약·촉매·용매 1

HCID 86642925t-Butanol 2-butanone용매

반응 조건

온도
110 °C

실험 절차

6-bromonaphthalen-2-ol (CAS no. 15231-91-1) (3.0 g, 14.8 mmol, 1.0 eq.) was dissolved in a mixture of t-butanol/2-butanone (4 mL/2 mL). Then cesium carbonate (12 g, 37.2 mmol, 2.5 eq.) was added to the mixture and the mixture was stirred at 110° C. for 10 min. then trans-4-tert-butylcyclohexyl methanesulfonate (3.48 g, 16.2 mmol, 1.1 eq.) was added to the mixture. The suspension was stirred at 100° C. under a nitrogen atmosphere for 15 h. The reaction mixture was extracted with ethyl acetate and the organic layer was purified by silica gel column chromatography using petroleum ether as eluent to give 2-bromo-6-(trans-4-tert-butylcyclohexyloxy)naphthalene as a slight yellow solid (1.7 g, yield: 32%). ESI-MS: 361.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.89 (s, 1H), 7.63 (d, 1H), 7.56 (d, 1H), 7.47 (d, 1H), 7.15-7.11 (m, 2H), 4.26-4.24 (m, 1H), 2.27-2.25 (m, 2H), 1.89-1.87 (m, 2H), 1.45-1.09 (m, 5H), 0.89 (s, 9H).

후처리

  1. stirringThe suspension was stirred at 100° C. under a nitrogen atmosphere for 15 h
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. customthe organic layer was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-a0b3bc6b1d7b4d0e89c93a9f94caea99
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09186367B2

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