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

HRID 716467ノート

反応式

HRID 716467 の反応式
[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].[C:21]([C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[C:30]([CH3:38])[CH:31]2[Si:34](Cl)([CH3:36])[CH3:35])=[C:27]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:41][CH:40]=2)[C:26]=1[O:49][CH3:50])([CH3:24])([CH3:23])[CH3:22].O>CCOCC.C([Cu])#N>[C:21]([C:25]1[CH:33]=[C:32]2[C:28]([CH:29]=[C:30]([CH3:38])[CH:31]2[Si:34]([CH:16]2[C:15]3[C:19](=[C:11]([C:8]4[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=4)[CH:12]=[CH:13][CH:14]=3)[CH:18]=[C:17]2[CH3:20])([CH3:36])[CH3:35])=[C:27]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([CH3:48])([CH3:47])[CH3:46])=[CH:41][CH:40]=2)[C:26]=1[O:49][CH3:50])([CH3:24])([CH3:23])[CH3:22]

参加物

6

反応物 3

HCID 962WaterHCID 103553602-Methyl-7-(4'-tert-butylphenyl)indeneHCID 71231029[6-tert-Butyl-4-(4-tert-butylphenyl)-5-methoxy-2-methyl-1H-inden-1-yl](chloro)dimethylsilane

生成物 1

HCID 90314792[6-tert-Butyl-4-(4-tert-butylphenyl)-5-methoxy-2-methyl-1H-inden-1-yl][4-(4-tert-butylphenyl)-2-methyl-1H-inden-1-yl]dimethylsilane収率 100.4%

試薬・触媒・溶媒 2

HCID 178418546HCID 178418546、化合物触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a solution of 7.88 g (30.0 mmol) of 7-(4-tert-butylphenyl)-2-methyl-1H-indene in 200 ml of ether 12.0 ml (30.0 mmol) of 2.5 MnBuLi in hexanes was added in one portion at −40° C. This mixture was stirred overnight at room temperature, then cooled to −40° C., and 215 mg of CuCN was added. The resulting mixture was stirred for 1 h at −20° C., then cooled to −40° C., and a solution 13.2 g (30.0 mmol) of [6-tert-butyl-4-(4-tert-butylphenyl)-5-methoxy-2-methyl-1H-inden-1-yl](chloro)dimethylsilane (prepared as described above) in 150 ml of ether was added in one portion. Further on, this mixture was stirred overnight at ambient temperature, then 0.5 ml of water were added. This solution was filtered through a pad of silica gel 60 (40-63 um) which was additionally washed by 2×75 ml of dichloromethane. The combined organic elute was evaporated to dryness, and the residue was dried in vacuum. This procedure gave 20.1 g of the title product (on the evidence of NMR spectroscopy, it has ca. 90% purity and is a ca. 1:1 mixture of the distereomers) as yellowish glass which was further used without an additional purification.

後処理

  1. temperaturecooled to −40° C.
  2. stirringThe resulting mixture was stirred for 1 h at −20° C.
  3. temperaturecooled to −40° 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 2×75 ml of dichloromethane
  7. washThe combined organic elute
  8. customwas evaporated to dryness
  9. customthe residue was dried in vacuum

出典と根拠

ORDレコード
ord-060a156add6b4385a71717d353b17251
出典データセット
uspto-grants-2015_11
特許番号
US09187583B2

反応ノート

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