Water → (6-tert-Butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)[4-(4-tert-butylphenyl)-2-methyl-1H-inden-1-yl]dimethylsilane

HRID 716446Notes

Reaction equation

HRID 716446 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:19]=2[CH2:18][C:17]([CH3:20])=[CH:16]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[C:26]([C:30]1[CH:38]=[C:37]2[C:33]([CH:34]=[C:35]([CH3:43])[CH:36]2[Si:39](Cl)([CH3:41])[CH3:40])=[C:32]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:31]=1[O:50][CH3:51])([CH3:29])([CH3:28])[CH3:27].O>CCOCC.C([Cu])#N>[C:26]([C:30]1[CH:38]=[C:37]2[C:33]([CH:34]=[C:35]([CH3:43])[CH:36]2[Si:39]([CH:16]2[C:15]3[C:19](=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=4)[CH:12]=[CH:13][CH:14]=3)[CH:18]=[C:17]2[CH3:20])([CH3:41])[CH3:40])=[C:32]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:31]=1[O:50][CH3:51])([CH3:27])([CH3:28])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 103553602-Methyl-7-(4'-tert-butylphenyl)indeneHCID 71231037(6-tert-Butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 71231019(6-tert-Butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)[4-(4-tert-butylphenyl)-2-methyl-1H-inden-1-yl]dimethylsilaneYield 91%

Reagents, catalysts & solvents 2

HCID 178418546HCID 178418546, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 11.5 g (43.8 mmol) of 7-(4-tert-butylphenyl)-2-methyl-1H-indene in 300 ml of ether, 17.0 ml (42.5 mmol) of 2.5 M nBuLi in hexanes was added in one portion at −78° C. This mixture was stirred overnight at room temperature, then cooled to −60° C., and 150 mg of CuCN was added. The resulting mixture was stirred for 1 h at −20° C., then cooled to −70° C., and 16.2 g of (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)-dimethylsilane (42.08 mmol) in 150 ml of ether was added. Further on, this mixture was stirred overnight at ambient temperature, then 0.5 ml of water was added. This solution was filtered through a pad of silica gel 60 (40-63 um) which was additionally washed by dichloromethane. The combined organic elute was evaporated to dryness, and the obtained yellowish oil was purified by flash chromatography on silica gel 60 (40-63 um; eluent: hexane-dichloromethane, from 10:1 to 3:1, vol.). This procedure gave 23.4 g (91%) of the title compound as yellowish glass.

Workup

  1. temperaturecooled to −60° C.
  2. stirringThe resulting mixture was stirred for 1 h at −20° C.
  3. temperaturecooled to −70° C.
  4. stirringFurther on, this mixture was stirred overnight at ambient temperature
  5. filtrationThis solution was filtered through a pad of silica gel 60 (40-63 um) which
  6. washwas additionally washed by dichloromethane
  7. washThe combined organic elute
  8. customwas evaporated to dryness
  9. customthe obtained yellowish oil was purified by flash chromatography on silica gel 60 (40-63 um; eluent: hexane-dichloromethane, from 10:1 to 3:1, vol.)

Sources & evidence

ORD record
ord-de511c33130446998b278be02ccd6341
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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