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 716467노트

반응식

HRID 716467 반응식
[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]

참가 물질

6

반응물 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

생성물 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]dimethylsilane수율 100.4%

시약·촉매·용매 2

HCID 178418546HCID 178418546, 화합물촉매HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-060a156add6b4385a71717d353b17251
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187583B2

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