Tetrahydrofuran → Silane, (chloromethyl)(4-ethoxyphenyl)dimethyl-

HRID 977913

Reaction equation

HRID 977913 reaction equation
C1COCC1.Br[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1.[Cl:16][CH2:17][Si:18](Cl)([CH3:20])[CH3:19].C([Li])CCC>O.C(OCC)(=O)C>[Cl:16][CH2:17][Si:18]([CH3:20])([CH3:19])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH3:15])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 685234-BromophenetoleHCID 74393Silane, chloro(chloromethyl)dimethyl-HCID 178418339Butyllithium

Product 1

HCID 184717Silane, (chloromethyl)(4-ethoxyphenyl)dimethyl-Yield 49.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of 60 ml of THF, p-bromophenetole (9.7 gram) and chloromethyldimethylsilyl chloride (7.3 gram) was cooled in a dry ice/acetone bath. To the mixture was dropwise added 33 ml of 1.55M n-butyl lithium under an argon atmosphere. After stirring the mixture for additional 15 minutes at -78° C., the stirring was continued at room temperature for 30 minutes. The mixture was added with 6 ml of ethyl acetate and 30 ml of water, and extracted with ethyl ether. The ether extract was washed with saturated sodium chloride solution, dried, and concentrated. Distillation of the residue gave 5.5 gram of chloromethyldimethyl(4-ethoxyphenyl)silane. Physicochemical data of the product is listed in Table 3.

Workup

  1. temperaturewas cooled in a dry ice/acetone bath
  2. waitthe stirring was continued at room temperature for 30 minutes
  3. extractionextracted with ethyl ether
  4. extractionThe ether extract
  5. washwas washed with saturated sodium chloride solution
  6. customdried
  7. concentrationconcentrated
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-b1065096d3b94e748a4c45e61f4fe559
Source dataset
uspto-grants-1987_05
Patent number
US04663314

Linked notes

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