Toluene → [6-tert-Butyl-4-(3,5-di-tert-butylphenyl)-5-methoxy-2-methyl-1H-inden-1-yl](chloro)-dimethylsilane

HRID 716470Notes

Reaction equation

HRID 716470 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([C:16]3[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:19]=[C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:17]=3)[C:13]=1[O:14][CH3:15])[CH2:10][C:9]([CH3:30])=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.[Li]CCCC.[Cl:43][Si:44](Cl)([CH3:46])[CH3:45]>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]2[C:11]([CH:10]=[C:9]([CH3:30])[CH:8]2[Si:44]([Cl:43])([CH3:46])[CH3:45])=[C:12]([C:16]2[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:19]=[C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:17]=2)[C:13]=1[O:14][CH3:15])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6398DichlorodimethylsilaneHCID 712317445-tert-Butyl-7-(3,5-di-tert-butylphenyl)-6-methoxy-2-methyl-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 71231057[6-tert-Butyl-4-(3,5-di-tert-butylphenyl)-5-methoxy-2-methyl-1H-inden-1-yl](chloro)-dimethylsilaneYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 15.7 g (38.8 mmol) of 5-tert-butyl-7-(3,5-di-tert-butylphenyl)-6-methoxy-2-methyl-1H-indene in 200 ml of toluene 16.0 ml (40.0 mmol) of 2.5 M nBuLi in hexanes was added at room temperature. The resulting viscous solution was stirred for 10 h, and then 10 ml of THF was added. This mixture was stirred for 2 h at 60° C., then cooled to −20° C., and 25.0 g (194 mmol, 5 eq.) of dichlorodimethylsilane was added in one portion. The resulting solution was refluxed for 2 h, then evaporated to ca. ¾ of its volume, and filtered through glass frit (G3). The precipitate was additionally washed by 2×30 ml of toluene. The combined filtrate was evaporated to dryness to give 19.2 g (99%) of white solid which was further used without an additional purification.

Workup

  1. stirringThis mixture was stirred for 2 h at 60° C.
  2. temperatureThe resulting solution was refluxed for 2 h
  3. customevaporated to ca. ¾ of its volume
  4. filtrationfiltered through glass frit (G3)
  5. washThe precipitate was additionally washed by 2×30 ml of toluene
  6. customThe combined filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-3aaaa3a8f5bb4ebb90c14aa966bbc226
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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