Ethanol → HCID 70617822, compound

HRID 1606292Notes

Reaction equation

HRID 1606292 reaction equation
[CH3:1][O:2][C:3]1[C:20]2[C@@H:19]3[C@@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:21])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:22][CH3:23])[CH:4]=1.[CH2:24]([OH:26])[CH3:25].C1COCC1.[BH4-].[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:20]2[C@@H:19]3[C@@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C@@H:14]([O:21][C:24](=[O:26])[CH3:25])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]([O:22][CH3:23])[CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 68147558HCID 68147558, compound

Product 1

HCID 70617822HCID 70617822, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 60 mg. of rac.-1,3-dimethoxy-8α-estra-1,3,5(10)-trien-17-one in 3 ml. of ethanol and 1.0 ml. of THF is gradually combined at room temperature with 60 mg. of NaBH4 and agitated for 30 minutes under N2 and at room temperature. The reaction mixture is neutralized with glacial acetic acid, concentrated, taken up in ether, washed neutral with saturated NaCl solution, dried, and evaporated. The residue is dissolved in 1 ml. of pyridine, the solution is mixed with 0.5 ml. of acetic anhydride and maintained for 1 hour at 80° C. under N2. After cooling, the mixture is introduced into ice water; the precipitate is filtered off and taken up in ether. The ether solution is washed neutral with saturated NaCl solution, dried, and evaporated. Recrystallization from methanol over carbon yields 42 mg. of product, m.p. 131°-134° C.

Workup

  1. customis gradually combined at room temperature with 60 mg
  2. concentrationconcentrated
  3. washwashed neutral with saturated NaCl solution
  4. customdried
  5. customevaporated
  6. dissolutionThe residue is dissolved in 1 ml
  7. additionof pyridine, the solution is mixed with 0.5 ml
  8. temperatureAfter cooling
  9. additionthe mixture is introduced into ice water
  10. filtrationthe precipitate is filtered off
  11. washThe ether solution is washed neutral with saturated NaCl solution
  12. customdried
  13. customevaporated
  14. customRecrystallization from methanol over carbon
  15. customyields 42 mg

Sources & evidence

ORD record
ord-0245fcdd8d2e43148acb64ae9d9c8039
Source dataset
uspto-grants-1976_04
Patent number
US03951959

Reaction notes

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