Reaction #11402

ord-4e7fa853fe9144349445c73f356f4216

Reaction equation

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O
oestrone
CC(=O)[O-]
acetate
II
iodine
→
COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
2-methoxy-estrone
Yield 56.0%

Reactants

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CCC2=O
oestrone
CC(=O)[O-]
acetate
II
iodine
—
2-iodo-estrone

Reagents

[Cl][Cu][Cl]
copper chloride

Solvents

CC(=O)O
acetic acid

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherafter successive recrystallizations
  2. 2
    Other2-Iodo-estrone then reacted with a large excess of a freshly prepared solution of sodium methoxyde

Procedure

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07098218B2uspto-grants-2006_08