Formic Acid → 3beta-Formyloxy-androstene-17-one

HRID 356587

Reaction equation

HRID 356587 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.O.[CH:23](O)=[O:24]>>[CH:23]([O:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[CH:14]([CH2:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH:8]=[CH:9][C:10]2=[O:11])[CH2:19]1)=[O:24]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 5881Dehydroepiandrosterone

Product 1

HCID 1317209413beta-Formyloxy-androstene-17-one

Conditions

Temperature
60 °C

Procedure

Following the procedure described by Ringold (H. J. Ringold, et al., J. Am. Chem. Soc. 78, 816, 1956), dehydroepiandrosterone (2.88 g, 10 mmol) dissolved in 85% formic acid (100 mL) is heated at 60° C. for 1 h. After cooling, the mixture is poured into iced water and after 16 h, crystals are filtered and dried in vacuo.

Workup

  1. temperatureAfter cooling
  2. filtrationcrystals are filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-c23a8e0841a64406bce4926a92eaf7b2
Source dataset
uspto-grants-1998_11
Patent number
US05837700

Linked notes

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