2,8-bis((tert-butyldimethylsilyl)oxy)chromeno[4,3-c]chromen-5(11H)-one → 2-[4-{-1-[4-(2-azepan-1-yl-ethoxy)-phenyl]-1-hydroxy-ethyl}-7-(tert-butyl-dimehyl-silyloxy)-2H-chromen-3-yl]-5-(tert-butyl-dimethyl-silyloxy)-phenol

HRID 2214297노트

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HRID 2214297 반응식
Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH2:18]([Li])CCC.[C:23]([Si:27]([CH3:57])([CH3:56])[O:28][C:29]1[CH:30]=[CH:31][C:32]2[C:33]3[C:46](=[O:47])[O:45][C:44]4[CH:43]=[C:42]([O:48][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])[CH:41]=[CH:40][C:39]=4[C:34]=3[CH2:35][O:36][C:37]=2[CH:38]=1)([CH3:26])([CH3:25])[CH3:24].C[Mg]Br>C1COCC1>[N:9]1([CH2:8][CH2:7][O:6][C:5]2[CH:16]=[CH:17][C:2]([C:46]([C:33]3[C:32]4[C:37](=[CH:38][C:29]([O:28][Si:27]([C:23]([CH3:25])([CH3:24])[CH3:26])([CH3:56])[CH3:57])=[CH:30][CH:31]=4)[O:36][CH2:35][C:34]=3[C:39]3[CH:40]=[CH:41][C:42]([O:48][Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])=[CH:43][C:44]=3[OH:45])([OH:47])[CH3:18])=[CH:3][CH:4]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

참가 물질

6

반응물 4

HCID 115915722,8-bis((tert-butyldimethylsilyl)oxy)chromeno[4,3-c]chromen-5(11H)-oneHCID 130635441-[2-(4-Bromophenoxy)ethyl]azepaneHCID 178418339ButyllithiumHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 693277712-[4-{-1-[4-(2-azepan-1-yl-ethoxy)-phenyl]-1-hydroxy-ethyl}-7-(tert-butyl-dimehyl-silyloxy)-2H-chromen-3-yl]-5-(tert-butyl-dimethyl-silyloxy)-phenol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of 1-[2-(4-bromophenoxy)ethyl]-azepane (356 mg, 1.19 mmol) in THF (7.5 mL) at −78° C., was added n-butyl lithium (2.5 M in hexane, 466 μL, 1.17 mmol). The reaction mixture was stirred at −78° C. for 0.5 hours. To the mixture was then added 2,8-bis-(tert-butyl-dimethyl-silyloxy)-11H-chromeno[4,3-c]chromen-5-one, prepared as in Example 22, (149 mg, 0.29 mmol) in THF (3 mL) and the reaction mixture stirred at −78° C. for 1.5 hours. To the mixture was then methyl magnesium bromide (3 M in diethyl ether, 1 mL, 3 mmol) at −78° C. and then stirred at room temperature overnight. The reaction was quenched with aqueous NH4Cl and extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. The remaining solvent was evaporated to yield the crude title product as a yellow oil, which was carried on to the next step without further purification.

후처리

  1. stirringthe reaction mixture stirred at −78° C. for 1.5 hours
  2. customThe reaction was quenched with aqueous NH4Cl
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe remaining solvent was evaporated

출처 및 근거

ORD 기록
ord-c90e032c6e8840b0a4a40220f79f7ad5
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105679B2

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