반응 #422841
ord-5afa8f973f72433db71f7e61a9e160d4
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시약
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후처리
- 1기타the reaction mixture was quenched with MeOH (10 mL)
- 2농축concentrated
- 3추출was extracted with EtOAc (twice)
- 4세척The combined organic phase was washed with brine
- 5건조dried over Na2SO4
- 6농축concentrated in vaccuo
- 7기타to give the crude product
- 8기타Purification by silica gel chromatography
실험 절차
in THF (30 mL) was added n-BuLi (1.6 M. 5.8 mmol). After 30 minutes 4-(triisopropylsilyloxy)benzaldehyde (1.5 g, 5.3 mmol) in THF (2 mL) was added into the reaction mixture. The reaction mixture was warmed to room temperature and quenched with aq. NH4Cl. The water phase was extracted with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, and concentrated in vaccuo to provide the crude product. Purification by silica gel chromatography provide (4-chlorophenyl)(4-(triisopropylsilyloxy)phenyl)methanol (1.7 g, 4.2 mmol). (4-Chlorophenyl)(4-(triisopropylsilyloxy)phenyl)methanol (1.7 g, 4.2 mmol) was dissolved in THF (5 mL) and TBAF (1.0 M, 6.0 mmol) was added. After 15 minutes, the reaction mixture was quenched with MeOH (10 mL), concentrated, and the residue was purified by silica gel chromatography to afford4-((4-chlorophenyl)(hydroxy)methyl)phenol (963.1 mg, 4.1 mmol). This was subjected to alkylation with 1,8-dibromooctane (3.3 g, 12.3 mmol) and K2CO3 (1.7 g, 12.3 mmol) in DMF (45 mL). After 12h the reaction mixture was diluted with water (150 mL) and water phase was extracted with EtOAc (twice). The combined organic phase was washed with brine, dried over Na2SO4, and concentrated in vaccuo to give the crude product. Purification by silica gel chromatography provided (4-(8-bromooctyloxy)phenyl)(4-chlorophenyl)methanol (1.6 g, 3.7 mmol).