Potassium Carbonate → Tert-butyl(dimethyl)[(2-{[4-(trifluoromethoxy)phenoxy]methyl}-2-propenyl)oxy]silane

HRID 2066667노트

반응식

HRID 2066667 반응식
I[CH2:2][C:3](=[CH2:13])[CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[F:14][C:15]([F:25])([F:24])[O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:9]([Si:6]([CH3:8])([CH3:7])[O:5][CH2:4][C:3]([CH2:2][O:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:15]([F:14])([F:24])[F:25])=[CH:18][CH:19]=1)=[CH2:13])([CH3:12])([CH3:11])[CH3:10]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 11358863Tert-butyl(dimethyl)silyl 2-(iodomethyl)-2-propenyl ether

생성물 1

HCID 66955670Tert-butyl(dimethyl)[(2-{[4-(trifluoromethoxy)phenoxy]methyl}-2-propenyl)oxy]silane수율 58.2%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
50 °C

실험 절차

A mixture of iodide 165 (4.63 g, 14.8 mmol), 4-(trifluoromethoxy)phenol (3.10 mL, 23.9 mmol) and powdered K2CO3 (3.56 g, 25.8 mmol) in acetone (10 mL) was stirred at 50° C. for 11 h. The resulting cooled mixture was diluted with ice-water (100 mL) and extracted with CH2Cl2 (4×100 mL). The combined extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-3% CH2Cl2/petroleum ether firstly gave foreruns, and then further elution with 5-10% CH2Cl2/petroleum ether gave tert-butyl(dimethyl)[(2-{[4-(trifluoromethoxy)phenoxy]methyl}-2-propenyl)oxy]silane (166) (3.12 g, 58%) as a colourless oil; 1H NMR (CDCl3) δ 7.12 (br d, J=9.0 Hz, 2H), 6.90 (dt, J=9.1, 2.9 Hz, 2H), 5.27 (d, J=0.7 Hz, 1H), 5.20 (d, J=1.1 Hz, 1H), 4.54 (s, 2H), 4.24 (s, 2H), 0.91 (s, 9H), 0.07 (s, 6H); HRFABMS calcd for C17H26F3O3Si m/z [M+H]+ 363.1603. found 363.1604.

후처리

  1. temperatureThe resulting cooled mixture
  2. extractionextracted with CH2Cl2 (4×100 mL)
  3. customThe combined extracts were evaporated to dryness
  4. customthe residue was chromatographed on silica gel
  5. washElution with 0-3% CH2Cl2/petroleum ether firstly gave foreruns
  6. washfurther elution with 5-10% CH2Cl2/petroleum ether

출처 및 근거

ORD 기록
ord-437284d6566449988b6d308e5a93464c
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293734B2

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