Water → HCID 15718557, compound

HRID 373035Notes

Reaction equation

HRID 373035 reaction equation
C[O:2][C:3]1[CH2:4][C:5]2[CH2:6][CH2:7][C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]3[CH2:10][C@H:11]2[CH2:21][C@:12]21[O:22][CH3:23].S(=O)(=O)(O)O.O>CC(C)=O>[CH3:23][O:22][C@@:12]12[CH2:21][C@@H:11]1[CH2:10][C@H:9]1[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]21[CH3:14])[C:18]1[CH2:19][CH2:20][C:3](=[O:2])[CH2:4][C:5]=1[CH2:6][CH2:7]3

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 15718555HCID 15718555, compound

Product 1

HCID 15718557HCID 15718557, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 g of 3,17-dimethoxy-16alpha,17alpha-methylene-estra-2,5(10)-diene is suspended in 165 ml of 80% aqueous acetone and is mixed with vigorous stirring with 0.2 ml of 25% sulfuric acid. Then, with stirring, it is heated on the water bath (60° C.) until all the steroid has gone into solution (about 30 minutes). Then, it is allowed to cool to room temperature and stirred one more hour. After the reaction has been completed, the steroid is precipitated by the addition of water, separated and dried. 9.5 g of crystalline 16alpha,17alpha-methylene compound, which was used in the next step without recrystallization, is obtained.

Workup

  1. additionis mixed
  2. customhas gone into solution (about 30 minutes)
  3. stirringstirred one more hour
  4. customthe steroid is precipitated by the addition of water
  5. customseparated
  6. customdried
  7. custom9.5 g of crystalline 16alpha,17alpha-methylene compound, which was used in the next step without recrystallization
  8. customis obtained

Sources & evidence

ORD record
ord-b992b4f16fc2469a824462e54f035bdb
Source dataset
uspto-grants-1992_11
Patent number
US05162312

Reaction notes

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