Formaldehyde → 3Betahydroxymethoxy-5-androsten-17-one acetate

HRID 1459160Notes

Reaction equation

HRID 1459160 reaction equation
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[H-].[Na+].[C:24]([O:27]CCl)(=[O:26])[CH3:25].[C:30](Cl)(=[O:32])C.C=O>C1COCC1.[Cl-].[Cl-].[Zn+2].O>[C:24]([OH:27])(=[O:26])[CH3:25].[OH:32][CH2:30][O:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[C:14](=[CH:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:19]1

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 5881DehydroepiandrosteroneHCID 6367Acetyl chlorideHCID 24758Sodium hydride2×HCID 69366Chloromethyl acetate

Product 1

HCID 1317205663Betahydroxymethoxy-5-androsten-17-one acetate

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dehydroepiandrosterone (2.88 g, 10 mmol) in THF (100 mL) is added sodium hydride (11 mmol, 60% in oil) at room temperature under an argon atmosphere. When all the sodium hydride has reacted, chloromethyl acetate (prepared from acetyl chloride and formaldehyde (or derivative) using ZnCl2 as catalyst) is added and the mixture is heated for a few hours. After cooling, the mixture is poured into water and extracted with ethyl acetate. The organic phase is then washed with water, dried, filtered and evaporated to dryness to give the desired compound.

Workup

  1. additionis added
  2. temperaturethe mixture is heated for a few hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is then washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-f4da17270272404180420ac72c280e0e
Source dataset
uspto-grants-1998_12
Patent number
US05854229

Reaction notes

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