Toluene → Ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)-naphth-7-yl]naphth-2-oate

HRID 1377

반응식

HRID 1377 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](C(OCC)=O)=[CH:7][CH:6]=[CH:5]2.[C:17](=[O:20])([O-])[O-:18].[Na+].[Na+].[CH3:23][C:24]1([CH3:45])[CH2:33][CH2:32][CH:31]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[C:30]2[CH:29]=[C:28](B(O)O)[CH:27]=[CH:26][C:25]1=2.[C:46]1(C)C=CC=C[CH:47]=1>CO>[CH2:46]([O:18][C:17]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:32]3[CH:31]([O:34][Si:35]([C:38]([CH3:39])([CH3:40])[CH3:41])([CH3:37])[CH3:36])[C:30]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:24]([CH3:23])([CH3:45])[CH2:33]3)[CH:3]=2)[CH:8]=1)=[O:20])[CH3:47]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 22571499(5,6,7,8-Tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)naphth-2-yl)boronic acidHCID 22571542Ethyl 6-bromo-1-naphthoate

생성물 1

HCID 22571555Ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)-naphth-7-yl]naphth-2-oate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
90 °C

실험 절차

To a degassed solution of 722 mg (2.6 mmol) of ethyl 6-bromo-naphthalenecarboxylate in 6.0 mL of toluene, was added sequentially 90 mg (0.08 mmol) of tetrakis-triphenylphosphine palladium (O), 5.0 mL (10.0 mmol) of 2M sodium carbonate, and a solution of 1.018 g (3.1 mmol) of (5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)naphth-2-yl)boronic acid (Compound B14) in 3.0 mL of MeOH. The reaction was heated at 90° C. for 15 h. The reaction was diluted with 2N Na2 CO3, and extracted with CH2Cl2 (2×), the organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an oil. The crude product was purified flash chromatography (silica, 5% ethyl acetate in hexane) to afford the title compound as a white solid.

후처리

  1. additionThe reaction was diluted with 2N Na2 CO3
  2. extractionextracted with CH2Cl2 (2×)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give an oil
  7. customThe crude product was purified flash chromatography (silica, 5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-9be964bec0914ee8a55f4080f106b48c
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723666

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