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

HRID 2090131

Reaction equation

HRID 2090131 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-a8faa88cdc2548909b756d50eebce45f
Source dataset
uspto-grants-2013_05
Patent number
US08436133B2

Linked notes

Loading…