Hydrochloric Acid → 21-Chloromethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973735Notes

Reaction equation

HRID 1973735 reaction equation
[OH:1][C@@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[C:18](=[O:24])[CH2:17][C@@:16]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:15])[CH:13]=[CH2:14])[CH2:3]1.[ClH:26].O>O1CCOCC1>[Cl:26][CH2:14][CH2:13][C:12](=[O:15])[C@@H:11]1[C@:16]2([CH3:25])[C@H:8]([C@H:7]3[C@H:19]([C:18](=[O:24])[CH2:17]2)[C@:20]2([CH3:23])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:22][CH2:21]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86734286HCID 86734286, compound

Product 1

HCID 8673430721-Chloromethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3α-Hydroxy-21-methylene-5α-pregnane-11,20-dione (500 mg) was dissolved in dioxan (40 ml) and dry hydrogen chloride passed through the solution for 1 hour. The mixture was left to stand for a further 2 hours, then poured into water and the sticky solid extracted into ether. The extracts were washed with saturated sodium bicarbonate, water and then dried over anhydrous sodium sulphate. After evaporation and trituration of the resulting foam with ether/petrol the title compound (375 mg) was obtained as a white solid. m.p. 110°-112° with gas evolution [α]D + 100° (c = 1.06).

Workup

  1. waitThe mixture was left
  2. extractionthe sticky solid extracted into ether
  3. washThe extracts were washed with saturated sodium bicarbonate, water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customAfter evaporation and trituration of the resulting foam with ether/petrol the title compound (375 mg)
  6. customwas obtained as a white solid
  7. custom100° (c = 1.06)

Sources & evidence

ORD record
ord-80e6cf0b5f6b4509a8f02115f79cdaf6
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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