تفاعل #11402

معادلة التفاعل

oestrone

acetate

iodine

→

2-methoxy-estrone

المردود 56.0%

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   أخرىafter successive recrystallizations
2. 2
   أخرى2-Iodo-estrone then reacted with a large excess of a freshly prepared solution of sodium methoxyde

الإجراء التجريبي

To this end, 2-iodo-estrone 49 was prepared by treating oestrone with mercuric-acetate and iodine in acetic acid.40 The selective halogenation at position 2 was complete within 2 hours at room temperature with an overall yield of 56% after successive recrystallizations. 2-Iodo-estrone then reacted with a large excess of a freshly prepared solution of sodium methoxyde, in presence of copper chloride in refluxing pyridine41 and gave 2-methoxy-estrone 50 with a yield: of 75%. This method has the advantage of not involving any protecting group and gives good overall yield (42%) for the synthesis of 2-methoxy-estrone in two steps from oestrone.

المصدر