Dichlorodimethylsilane → (6-tert-Butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane

HRID 716444Notes

Reaction equation

HRID 716444 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13]=1[O:14][CH3:15])[CH2:10][C:9]([CH3:22])=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.C1COCC1.[Cl:33][Si:34](Cl)([CH3:36])[CH3:35]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]2[C:11]([CH:10]=[C:9]([CH3:22])[CH:8]2[Si:34]([Cl:33])([CH3:36])[CH3:35])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]=1[O:14][CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6398DichlorodimethylsilaneHCID 8028TetrahydrofuranHCID 602106945-tert-butyl-6-methoxy-2-methyl-7-phenyl-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 71231037(6-tert-Butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilaneYield 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 16.2 g (55.4 mmol) of 5-tert-butyl-6-methoxy-2-methyl-7-phenyl-1H-indene in 300 ml of toluene, 22.2 ml (55.5 mmol) of 2.5 M nBuLi in hexanes was added at room temperature. The resulting viscous solution was stirred for 2 h, and then 15 ml of THF was added. The formed suspension was stirred for 12 h at room temperature, ca. 2 h at 60° C., then cooled to −20° C., and 35.8 g (277 mmol) of dichlorodimethylsilane was added in one portion. The resulting solution was warmed to 60° C. and stirred for 1 h at this temperature. The resulting mixture was evaporated to ca. ½ of its volume, then filtered through glass frit (G3). The precipitate was additionally washed by 20 ml of toluene. The combined filtrate was evaporated to dryness to give 21.2 g (99%) of viscous yellowish oil.

Workup

  1. stirringThe formed suspension was stirred for 12 h at room temperature, ca. 2 h at 60° C.
  2. temperatureThe resulting solution was warmed to 60° C.
  3. stirringstirred for 1 h at this temperature
  4. customThe resulting mixture was evaporated to ca. ½ of its volume
  5. filtrationfiltered through glass frit (G3)
  6. washThe precipitate was additionally washed by 20 ml of toluene
  7. customThe combined filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-4a7fa270ed5b428fa26c0db63f1c6301
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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