Boron trifluoride → trans-3-Allyloxy-4-hydroxytetrahydrofuran

HRID 370316

반응식

HRID 370316 반응식
[O:1]1[CH:6]2[CH:2]1[CH2:3][O:4][CH2:5]2.[CH2:7]([OH:10])[CH:8]=[CH2:9].B(F)(F)F>ClCCl>[CH2:7]([O:10][C@H:6]1[C@H:2]([OH:1])[CH2:3][O:4][CH2:5]1)[CH:8]=[CH2:9]

참가 물질

5

반응물 3

HCID 6356Boron trifluorideHCID 7858Allyl AlcoholHCID 675113,6-Dioxabicyclo[3.1.0]hexane

생성물 1

HCID 11435015trans-3-Allyloxy-4-hydroxytetrahydrofuran

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a 10-L flask fitted with a double surface condenser, overhead stirrer and nitrogen inlet was added 3,4-epoxytetrahydrofuran (750 g, 8.71 mol), dichloromethane (3750 ml, 5 vol) and allyl alcohol (2530 g, 43.56 mol, 5 eq.). The solution was cooled to between 0° and 5° C. and boron trifluoride diethyletherate (61.8 g, 0.436 mol, 0.05 eq.) was added dropwise whilst maintaining the temperature below 10° C. After addition was complete the solution was allowed to warm to room temperature at which point the reaction slowly exothermed to reflux. After 3 hours 1H NMR analysis showed that no epoxide remained and the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution (1500 mL, 2 vol). The phases were separated and the organic phase was washed with a further portion of saturated aqueous sodium hydrogen carbonate solution (1500 mL, 2 vol). The combined aqueous washes were extracted with CH2Cl2 (5×750 ml, 1 vol). After drying the organic phases over MgSO4, filtering and concentrating in vacuo, the trans-3-allyloxy-4-hydroxytetrahydrofuran (I) was isolated by reduced pressure distillation (bp 94° C. @ 3 mbar) to give 1004.0 g (79.9% yield) of a clear colorless liquid.

후처리

  1. customTo a 10-L flask fitted with a double surface condenser, overhead stirrer and nitrogen inlet
  2. temperatureThe solution was cooled to between 0° and 5° C.
  3. temperaturewhilst maintaining the temperature below 10° C
  4. additionAfter addition
  5. customthe reaction
  6. temperatureto reflux
  7. customthe reaction was quenched with saturated aqueous sodium hydrogen carbonate solution (1500 mL, 2 vol)
  8. customThe phases were separated
  9. washthe organic phase was washed with a further portion of saturated aqueous sodium hydrogen carbonate solution (1500 mL, 2 vol)
  10. extractionThe combined aqueous washes were extracted with CH2Cl2 (5×750 ml, 1 vol)
  11. dry with materialAfter drying the organic phases over MgSO4
  12. filtrationfiltering
  13. concentrationconcentrating in vacuo

출처 및 근거

ORD 기록
ord-8694fbb9078a4f299750306a80b215ba
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140516

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