Реакция #95332

ord-fcb22ce1c5ff443d9bbd1c9b02ab2206

Уравнение реакции

CCC[C@]1(OC(C)=O)CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)C[C@H](C)[C@]4(C)[C@H]3CC[C@@]21C
17β-acetoxy-1α-methyl-17α-n-propyl-5α-androstan-3β-ol
COCOC
formaldehyde dimethylacetal
O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3
phosphorus pentoxide
→
CCC[C@]1(OC(C)=O)CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](OCOC)C[C@H](C)[C@]4(C)[C@H]3CC[C@@]21C
17β-acetoxy-3β-methoxymethoxy-1α-methyl-17α-n-propyl-5α-androstane

Реактанты

CCC[C@]1(OC(C)=O)CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)C[C@H](C)[C@]4(C)[C@H]3CC[C@@]21C
17β-acetoxy-1α-methyl-17α-n-propyl-5α-androstan-3β-ol
COCOC
formaldehyde dimethylacetal
O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3
phosphorus pentoxide

Реагенты

Нет

Растворители

ClCCl
dichloromethane

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Промывкаwashed with dichloromethane containing 3-5% triethylamine
  2. 2
    ДругоеThe crude product obtained
  3. 3
    Другоеafter evaporation
  4. 4
    Другоеis chromatographed on silica gel

Методика

400 mg of 17β-acetoxy-1α-methyl-17α-n-propyl-5α-androstan-3β-ol is combined in 2.8 ml of absolute dichloromethane and 1.8 ml of formaldehyde dimethylacetal with a mixture of 600 mg of kieselguhr W 20 and 300 mg of phosphorus pentoxide and stirred for 45 minutes at room temperature. The mixture is vacuumfiltered from the insoluble components and washed with dichloromethane containing 3-5% triethylamine. The crude product obtained after evaporation is chromatographed on silica gel, thus producing 280 mg of 17β-acetoxy-3β-methoxymethoxy-1α-methyl-17α-n-propyl-5α-androstane.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04344941uspto-grants-1982_08