Ammonia → HCID 69917769, compound

HRID 1837032Notes

Reaction equation

HRID 1837032 reaction equation
[CH2:1]([C@@H:3]1[CH2:20][C:19]2[CH:18]=[C:17]([O:21][CH3:22])[CH:16]=[CH:15][C:14]=2[C@@H:13]2[C@@H:4]1[C:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:23])[CH2:7][CH:6]=1)[CH3:2].[Li].N.CC(O)C>O1CCCC1>[CH2:1]([C@@H:3]1[CH2:20][C:19]2[CH2:18][C:17]([O:21][CH3:22])=[CH:16][CH2:15][C:14]=2[C@@H:13]2[C@@H:4]1[C:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:23])[CH2:7][CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 3776IsopropanolHCID 3028194LithiumHCID 69625181HCID 69625181, compound

Product 1

HCID 69917769HCID 69917769, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-35 °C

Procedure

x)—The alcohol obtained in the previous step (1.5 g) in dry tetrahydrofuran (24 ml) was added to a refluxing solution of lithium (2.12 g) in liquid ammonia (98 ml). After 4.5 h stirring at −35° C., 2-propanol was added in 30 min. and the ammonia was allowed to evaporate. Water was added and the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure, to give (7α,17β)-7-ethyl-3-methoxyestra-2,5(10),14-trien-17-ol (1.65 g). The product was used in the following step without further purification.

Workup

  1. customto evaporate
  2. additionWater was added
  3. extractionthe product was extracted into ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dab65b03205b4e55b245ffd47a87b3ea
Source dataset
uspto-grants-2004_08
Patent number
US06780854B2

Reaction notes

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