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

HRID 1377

反应方程式

HRID 1377 反应方程式
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]

参与物

6

反应物 4

HCID 1140甲苯HCID 10340Carbonic acid sodium salt (1:2)HCID 22571499(5,6,7,8-Tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)naphth-2-yl)boronic acidHCID 22571542Ethyl 6-bromo-1-naphthoate

产物 1

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

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

反应条件

温度
90 °C

实验过程

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.

后处理

  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)

来源与证据

ORD记录
ord-9be964bec0914ee8a55f4080f106b48c
来源数据集
uspto-grants-1998_03
专利号
US05723666

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