تفاعل #2205

ord-5e3cc0d24c92424b96fce5ec22cba17e

معادلة التفاعل

OCC#CCO
2-butyne-1,4-diol
C1=COCCC1
3,4-dihydro-2H-pyran
OCC#CCOC1CCCCO1
4-tetrahydropyranoxy-2-butyn-1-ol
المردود 68.8%

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONof p-toluenesulfonic add
  2. 2
    أخرىwas evaporated
  3. 3
    workup.ADDITIONthe residue was poured into 200 ml of water
  4. 4
    استخلاصThe aqueous solution was extracted with hexane (2×100 ml)
  5. 5
    استخلاصre-extracted with ether (3×100 ml)
  6. 6
    غسيلThe combined ether extracts were washed with 100 ml of brine
  7. 7
    تجفيفdried over magnesium sulfate
  8. 8
    أخرىevaporated

الإجراء التجريبي

To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic add and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05728698uspto-grants-1998_03