Chlorotrimethylsilane → Silane, [(3,4-dihydro-2-naphthalenyl)oxy]trimethyl-

HRID 981827Notes

Reaction equation

HRID 981827 reaction equation
[CH2:1]1[C:10](=[O:11])[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.C(N(CC)CC)C.[CH3:19][Si:20](Cl)([CH3:22])[CH3:21]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:19][Si:20]([CH3:22])([CH3:21])[O:11][C:10]1[CH2:1][CH2:2][C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 682662-Tetralone

Product 1

HCID 11042217Silane, [(3,4-dihydro-2-naphthalenyl)oxy]trimethyl-

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Charge an oven dried, nitrogen flushed 100-mL round bottomed flask equipped with a stirring bar with β-tetralone (4.977 grams, 0.0340 moles), triethylamine (6.970 grams, 0.0689 moles), 4-dimethylamino pyridine (0.219 grams,0.0018 moles), trimethylsilyl chloride (7.704 grams, 0.0709 moles) and 30 mL methylene chloride. Stir at RT for 20 hours, filter, wash the solid with 1×20 mL methylene chloride, wash the combined organic layers with 1×5 mL saturated sodium bicarbonate solution, 1×5 mL water, dry over magnesium sulfate, concentrate on a Buchi rotavapor and distill (96°-99° C., 1 Torr) to yield the product as a viscous oil.

Workup

  1. additionCharge an oven
  2. customdried
  3. customnitrogen flushed 100-mL round bottomed flask
  4. filtrationfilter
  5. washwash the solid with 1×20 mL methylene chloride
  6. washwash the combined organic layers with 1×5 mL saturated sodium bicarbonate solution, 1×5 mL water
  7. dry with materialdry over magnesium sulfate
  8. concentrationconcentrate on a Buchi rotavapor
  9. distillationdistill (96°-99° C., 1 Torr)

Sources & evidence

ORD record
ord-728400030152481b98ae22d3bd531cb3
Source dataset
uspto-grants-1991_02
Patent number
US04992591

Reaction notes

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