1,1',1''-(Chlorosilylidyne)tris(benzene) → 2-Methoxy-3-(triphenylsilyl)naphthalene

HRID 453921

반응식

HRID 453921 반응식
[Li]C(CC)C.CCCCCC.C1CCCCC1.[CH3:18][O:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1.[Si:30](Cl)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CN(C)P(N(C)C)(N(C)C)=O>O1CCCC1.O>[CH3:18][O:19][C:20]1[C:29]([Si:30]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:28][C:27]2[C:22]([CH:21]=1)=[CH:23][CH:24]=[CH:25][CH:26]=2

참가 물질

8

반응물 5

HCID 64581,1',1''-(Chlorosilylidyne)tris(benzene)HCID 71192-MethoxynaphthaleneHCID 12679HexamethylphosphoramideHCID 22494920Cyclohexane hexaneHCID 178418400CID 53628100

생성물 1

HCID 42290602-Methoxy-3-(triphenylsilyl)naphthalene수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 15.3 mL of sec-BuLi 1.3 M in hexane/cyclohexane (19.91 mmol) was added dropwise to a stirred solution of 3.0 g of 2-methoxynaphthalene (18.96 mmol) in 70 mL of tetrahydrofuran (THF) at a temperature of −30° C. and for a period of time of 15 min. After stirring overnight at room temperature, to the resultant tinted solution was added a solution of 5.87 g of Ph3SiCl (19.91 mmol) and 3.46 mL of hexamethylphosphoramide (HMPA) (19.88 mmol) in 50 mL of THF. The reaction mixture was heated at reflux for a period of time of 20 h, cooled and diluted with 500 mL of water. The organic part was extracted with 3 times 50 mL of Et2O. The combined organic extracts were dried over MgSO4, and evaporated. The crude residue was recrystallised from heptane and dried under vacuum to give 7.11 g of (3-methoxy-2-naphthyl)(triphenyl)silane (17.07 mmol) with a yield of 90%.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for a period of time of 20 h
  3. temperaturecooled
  4. extractionThe organic part was extracted with 3 times 50 mL of Et2O
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. customevaporated
  7. customThe crude residue was recrystallised from heptane
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-2024b7b8d9a84ea79dc3d5622c7a1778
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492493B2

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