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

HRID 716445Notes

Reaction equation

HRID 716445 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:13]=1)[CH2:10][C:9]([CH3:20])=[CH:8]2)([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:8]2[C:7]3[C:11](=[C:12]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:13]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=3)[CH:10]=[C:9]2[CH3:20])([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]

Participants

7

Reactant 4

HCID 962WaterHCID 71231037(6-tert-Butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilaneHCID 867279055-tert-butyl-2-methyl-7-phenyl-1H-indeneHCID 178418339Butyllithium

Product 1

HCID 71231013(6-tert-Butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)-(6-tert-butyl-2-methyl-4-phenyl-1H-inden-1-yl)dimethylsilaneYield 72.4%

Reagents, catalysts & solvents 2

HCID 178418546HCID 178418546, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 14.5 g (55.4 mmol) of 5-tert-butyl-2-methyl-7-phenyl-1H-indene in 400 ml of ether cooled to −78° C., 22.2 ml (55.5 mmol) of 2.5 M nBuLi in hexanes was added. This mixture was stirred overnight at room temperature, then cooled to −78° C., and 200 mg (2.23 mmol) of CuCN was added. The resulting mixture was stirred for 30 min at −20° C., then cooled to −78° C., and a solution of 21.2 g (55.4 mmol) of (6-tert-butyl-5-methoxy-2-methyl-4-phenyl-1H-inden-1-yl)(chloro)dimethylsilane in 200 ml of ether was added. This mixture was stirred overnight at room temperature, then 1 ml of water was added. The obtained mixture was passed through a short layer of silica gel 60 (40-63 um), the elute was evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-63 um; eluent: hexanes-dichloromethane=10:1, vol., then 3:1, vol.). This procedure gave 24.5 g (72%) of yellowish glassy solid.

Workup

  1. temperaturecooled to −78° C.
  2. stirringThe resulting mixture was stirred for 30 min at −20° C.
  3. temperaturecooled to −78° C.
  4. stirringThis mixture was stirred overnight at room temperature
  5. customthe elute was evaporated to dryness
  6. customThe product was isolated by flash-chromatography on silica gel 60 (40-63 um

Sources & evidence

ORD record
ord-60e8b199e9fb4a70a743494eda8effb2
Source dataset
uspto-grants-2015_11
Patent number
US09187583B2

Reaction notes

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