Chlorotrimethylsilane → (6-Methoxy-3,4-dihydronaphthalen-1-yloxy)-trimethylsilane

HRID 643912Notes

Reaction equation

HRID 643912 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21](=[O:25])[CH2:20][CH2:19][CH2:18]2.Cl[Si:27]([CH3:30])([CH3:29])[CH3:28]>C1COCC1.O>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[C:21]([O:25][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:20][CH2:19][CH2:18]2

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 141126-Methoxy-alpha-tetraloneHCID 178418339Butyllithium

Product 1

HCID 12705557(6-Methoxy-3,4-dihydronaphthalen-1-yloxy)-trimethylsilane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diisopropylamine (2.42 mL, 17.1 mmol) in THF (50 mL) at 0° C. is added n-BuLi (6.84 mL, 17.1 mmol, 2.5 M in hexane) dropwise. After 40 min, 6-methoxy-1-tetralone (3.0 g, 17.1 mmol) in THF (15 mL) is added at −78° C. It is then stirred at −78° C. for 2.5 h before chloro trimethylsilane (3.2 mL, 25.7 mmol) is added. It is then warmed to RT and stirred for 18 h. Water is added and the reaction mixture is extracted with EtOAc, washed with sat. NH4Cl solution, dried with MgSO4 and concentrated to give the title compound as a yellow oil. It is used in the next step without purification.

Workup

  1. additionis added
  2. extractionthe reaction mixture is extracted with EtOAc
  3. washwashed with sat. NH4Cl solution
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5602a2b644e7451296033e20ffd2fcbc
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

Loading…