反应 #11402

反应方程式

oestrone

acetate

iodine

→

2-methoxy-estrone

收率 56.0%

溶剂

acetic acid

反应条件

后处理

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

实验过程

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.

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