Ethylene Glycol → HCID 13055424, compound

HRID 848773Notes

Reaction equation

HRID 848773 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].CC1C=CC(S(O)(=O)=O)=CC=1.[OH:16][C@@:17]1([CH3:37])[CH2:22][CH2:21][C@H:20]2[C@H:23]3[C@H:33]([CH2:34][CH2:35][C@:18]12[CH3:19])[C@:31]1([CH3:32])[C@H:26]([CH2:27][C:28](=O)[CH2:29][CH2:30]1)[CH2:25][CH2:24]3>C(Cl)Cl>[CH2:1]1[O:4][C:28]2([CH2:29][CH2:30][C@@:31]3([CH3:32])[C@@H:26]([CH2:25][CH2:24][C@@H:23]4[C@@H:33]3[CH2:34][CH2:35][C@@:18]3([CH3:19])[C@H:20]4[CH2:21][CH2:22][C@@:17]3([OH:16])[CH3:37])[CH2:27]2)[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 10633Mestanolone

Product 1

HCID 13055424HCID 13055424, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethylene glycol (20 ml.) and p-TSA (5 mg.) is added to 17β-hydroxy-17α-methyl-5α-androstan-3-one (3.0 g.) in methylene chloride (20 ml.). The mixture is heated on a steam bath until most of the methylene chloride is removed. The remainder of the methylene chloride is removed on a rotary evaporator. The mixture is cooled and a small amount of a sodium bicarbonate solution and water are added and the mixture filtered. The filtered solids are washed and dried to give the subtitle compound, NMR (CDCl3), 0.83, 0.84, 1.20 and 3.92 δ.

Workup

  1. customis removed
  2. customThe remainder of the methylene chloride is removed on a rotary evaporator
  3. temperatureThe mixture is cooled
  4. additiona small amount of a sodium bicarbonate solution and water are added
  5. filtrationthe mixture filtered
  6. washThe filtered solids are washed
  7. customdried

Sources & evidence

ORD record
ord-011f554c1c5c4e2caf2f63fb67ab71ac
Source dataset
uspto-grants-1981_10
Patent number
US04297350

Reaction notes

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