Methanol → HCID 68148298, compound

HRID 1606297Notes

Reaction equation

HRID 1606297 reaction equation
C([O:4][C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([O:24]C(=O)C)[CH:6]=1)(=O)C.C(Cl)Cl.CO.Cl(O)(=O)(=O)=O>C(OCC)(=O)C>[OH:4][C:5]1[C:22]2[C@@H:21]3[C@@H:12]([C@H:13]4[C@@:17]([CH2:19][CH2:20]3)([CH3:18])[C:16](=[O:23])[CH2:15][CH2:14]4)[CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([OH:24])[CH:6]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 6344DichloromethaneHCID 24247Perchloric AcidHCID 68146911HCID 68146911, compound

Product 1

HCID 68148298HCID 68148298, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3 g. of 1,3-diacetoxy-8α-estra-1,3,5(10)-trien-17-one in 9 ml. of methylene chloride and 18 ml. of methanol is combined at 0° C. and under nitrogen with 0.23 ml. of perchloric acid (70%) in 1 ml. of methanol; the mixture is then agitated for 3 days at room temperature. Then, the mixture is diluted with ethyl acetate and washed neutral with saturated sodium chloride solution. After drying and evaporation, 2.9 g. of 1,3-dihydroxy-8α-estra-1,3,5(10)-trien-17-one is obtained as an oily substance.

Workup

  1. customis combined at 0° C. and under nitrogen with 0.23 ml
  2. washwashed neutral with saturated sodium chloride solution
  3. customAfter drying
  4. customevaporation, 2.9 g

Sources & evidence

ORD record
ord-69ffeaf018014d188bf982aa6c702689
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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