Water → Tert-butyl(4-(4-(4-((tert-butyldimethylsilyl)oxy)-3-ethoxyphenyl)-3-methylbut-3-en-1-yl)phenoxy)dimethylsilane

HRID 718543

反応式

HRID 718543 の反応式
[Br-].[Si:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:12][C:11]=1[O:36][CH2:37][CH3:38])([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[Li][CH2:40][CH2:41][CH2:42]C.[Si:44]([O:51][C:52]1[CH:57]=[CH:56][C:55]([CH2:58]CC(=O)C)=[CH:54][CH:53]=1)([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45].O>C1COCC1>[C:47]([Si:44]([O:51][C:52]1[CH:53]=[CH:54][C:55]([CH2:58][CH2:40][C:41]([CH3:42])=[CH:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][Si:2]([C:5]([CH3:6])([CH3:7])[CH3:8])([CH3:3])[CH3:4])=[C:11]([O:36][CH2:37][CH3:38])[CH:12]=2)=[CH:56][CH:57]=1)([CH3:45])[CH3:46])([CH3:48])([CH3:49])[CH3:50]

参加物

6

反応物 4

HCID 962WaterHCID 187986664-(4-tert-Butyldimethylsilyloxy-phenyl)-2-butanoneHCID 86702781(4-(tert-Butyldimethylsilyloxy)-3-ethoxyphenyl)methyltriphenylphosphonium bromideHCID 178418339Butyllithium

生成物 1

HCID 86702783Tert-butyl(4-(4-(4-((tert-butyldimethylsilyl)oxy)-3-ethoxyphenyl)-3-methylbut-3-en-1-yl)phenoxy)dimethylsilane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of (4-(tert-Butyldimethylsilyloxy)-3-ethoxyphenyl)methyltriphenyl-phosphonium bromide (28.7 g, 41.6 mmol, 1.0 equiv.) in THF (90 mL), was cooled to 0° C. After adding n-BuLi (1.6 M in hexanes, 26 mL, 41.6 mmol, 1.0 equiv.) at 0° C., the red suspension was stirred at 0° C. for 15 min. 4-(4-(Tert-butyldimethylsilyloxy)phenyl)butan-2-one (12.9 g, 41.6 mmol, 1.0 equiv.) in THF (30 mL) was added, and the mixture was stirred at 0° C.→70° C. for 16 h. After addition of H2O at 25° C., the aqueous layer was extracted with hexanes (2×), the combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 98:2) to give tert-butyl(4-(4-(4-((tert-butyldimethylsilyl)oxy)-3-ethoxyphenyl)-3-methylbut-3-en-1-yl)phenoxy)dimethylsilane as a colorless oil.

後処理

  1. stirringthe mixture was stirred at 0° C.→70° C. for 16 h
  2. extractionthe aqueous layer was extracted with hexanes (2×)
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash chromatography on SiO2 (cyclohexane/EtOAc 98:2)

出典と根拠

ORDレコード
ord-9aebf50cb9774e3a8e345e182f78c7cc
出典データセット
uspto-grants-2015_11
特許番号
US09193935B2

関連ノート

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