تفاعل #654072

ord-253a17a007a54d07b327bbadce7e74ee

معادلة التفاعل

C[C@H](CC=O)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3
aldehyde
C[C@H](CC=O)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3
(3β,5α,20R)-3-hydroxy-4,4,20-trimethylpregna-8,14-diene-21-carboxaldehyde
c1ccncc1
pyridine
O=C(Cl)c1ccccc1
Benzoyl chloride
→
C[C@H](CC=O)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](OC(=O)c2ccccc2)C(C)(C)[C@@H]1CC3
(3β,5α,20R)-3-(benzoyloxy)-4,4,20-trimethylpregna-8,14-diene-21-carboxaldehyde

المتفاعلات

C[C@H](CC=O)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3
aldehyde
C[C@H](CC=O)[C@H]1CC=C2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@@H]1CC3
(3β,5α,20R)-3-hydroxy-4,4,20-trimethylpregna-8,14-diene-21-carboxaldehyde
c1ccncc1
pyridine
O=C(Cl)c1ccccc1
Benzoyl chloride

الكواشف

لا شيء

المذيبات

O
water

ظروف التفاعل

درجة الحرارة
4°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGthe resulting mixture was stirred overnight
  2. 2
    استخلاصThe product was extracted into dichloromethane
  3. 3
    تركيزthe combined organic phases were concentrated under reduced pressure

الإجراء التجريبي

iv)—A solution of the aldehyde (12.3 g) mentioned above in dry pyridine (150 ml) was cooled to 4° C. Benzoyl chloride (8 ml) was added in 5 min. and the reaction mixture was stirred for 1.5 h at room temperature. Then it was poured into water (2 l) and the resulting mixture was stirred overnight. The product was extracted into dichloromethane and the combined organic phases were concentrated under reduced pressure to give (3β,5α,20R)-3-(benzoyloxy)-4,4,20-trimethylpregna-8,14-diene-21-carboxaldehyde (16.1 g). The product was used in the following step without further purification.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06177420B1uspto-grants-2001_01