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

HRID 718543

반응식

HRID 718543 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9aebf50cb9774e3a8e345e182f78c7cc
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193935B2

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