Water → 1-tert-Butoxy-3-fluoropropan-2-ol

HRID 1436919노트

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HRID 1436919 반응식
C(O)COCCOCCO.[FH:11].[F-].[K+].[C:14]([O:18][CH2:19][CH:20]1[CH2:22][O:21]1)([CH3:17])([CH3:16])[CH3:15].O>COC(C)(C)C>[C:14]([O:18][CH2:19][CH:20]([OH:21])[CH2:22][F:11])([CH3:17])([CH3:16])[CH3:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 8172Triethylene GlycolHCID 243142-((1,1-Dimethylethoxy)methyl)oxiraneHCID 11829350Potassium bifluoride

생성물 1

HCID 579396991-tert-Butoxy-3-fluoropropan-2-ol수율 61%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

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온도
130 °C

실험 절차

A 1.5 L 4-necked sulfonation flask equipped with magnetic stirring bar, reflux condenser, thermometer and an argon in/outlet, was charged with 333.3 mL triethylene glycol, 235.2 g (3.012 mol) finely ground potassium hydrogendifluoride and 200 g (1.536 mol) 2-tert-butoxymethyl-oxirane. The suspension was heated under stirring at an internal temperature of 130° C. for 7.5 h. The mixture was allowed to cool to RT over night, treated with 670 mL water and 350 mL tert-butyl methyl ether, the phases were separated and the aqueous phase was extracted with 350 ml tert-butyl methyl ether. The combined organic phases were washed with 350 mL brine, dried over sodium sulfate, filtered and evaporated. The brown oily residue (286 g) was distilled to provide 141 g (61%) 1-tert-butoxy-3-fluoro-propan-2-ol as colorless liquid, b.p. 80-93° C./70-40 mbar. GC composition: 1.1% 2-tert-butoxymethyl-oxirane, 95.1% 1-tert-butoxy-3-fluoro-propan-2-ol and 3.8% of 3-tert-butoxy-2-fluoro-propan-1-ol. 1H-NMR (CDCl3, 300 MHz): 4.45 (dxm, JH,F=46, —CH2—F); 3.93 (m, br, H—C(2); 3.45 (m, —CH2—O); 2.55 (d, br, J=6, OH); 1.20 (s, C(CH3)3).

후처리

  1. customA 1.5 L 4-necked sulfonation flask equipped with magnetic stirring bar
  2. temperaturereflux condenser
  3. temperatureThe suspension was heated
  4. temperatureto cool to RT over night
  5. customthe phases were separated
  6. extractionthe aqueous phase was extracted with 350 ml tert-butyl methyl ether
  7. washThe combined organic phases were washed with 350 mL brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. distillationThe brown oily residue (286 g) was distilled

출처 및 근거

ORD 기록
ord-bf32362a6bfa428aa89a7505c140dab8
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07619101B2

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