Acetone → HCID 66931861, compound

HRID 2382224Notes

Reaction equation

HRID 2382224 reaction equation
[BH4-].[Na+].[CH2:3]1[CH2:25][O:24][C:5]2([CH2:22][CH2:21][C:20]3[C:19]4[C@H:10]([C@H:11]5[C@@:15]([CH2:17][CH:18]=4)([CH3:16])[C:14](=[O:23])[CH2:13][CH2:12]5)[CH2:9][CH2:8][C:7]=3[CH2:6]2)[O:4]1.CC(C)=O.[Cl-].[Na+]>[OH-].[Na+].CO.C(OCC)(=O)C.O>[CH2:25]1[CH2:3][O:4][C:5]2([CH2:22][CH2:21][C:20]3[C:19]4[C@H:10]([C@H:11]5[C@@:15]([CH2:17][CH:18]=4)([CH3:16])[CH:14]([OH:23])[CH2:13][CH2:12]5)[CH2:9][CH2:8][C:7]=3[CH2:6]2)[O:24]1

Participants

9

Reactant 4

HCID 180AcetoneHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 7076399Estradiene dione-3-keta

Product 1

HCID 66931861HCID 66931861, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
2 °C

Procedure

Sodium borohydride (MW=37.8; 18.9 g; 500 mmol) dissolved in 0.5 N sodium hydroxide (100 ml) was introduced over about 5 min at around 2° C. into a suspension of 3,3-ethylenedioxyestra-5(10),9(11)-diene-17-one (MW=314.4; 100 g; 318 mmol) in methanol (1 liter). The medium was stirred for 2 h at around 2° C. and then acetone (100 ml) was introduced over about 15 min at around 5° C. The medium was stirred for 1 h, and poured at around 20° C. into the stirred mixture of water (2 liters), sodium chloride (500 g) and ethyl acetate (400 ml). The medium was separated by decantation and the aqueous phase was re-extracted with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate and concentrated at atmospheric pressure at 500 ml. The distillation is continued while the volume is kept constant by gradual introduction of 1,2-dimethoxyethane (DME). The temperature at the end of the exchange is 83° C. The solution was used as it is in the next step, but a dry extract gave the expected product (resin). C20H28O3; MW=316.4.

Workup

  1. stirringThe medium was stirred for 1 h
  2. customThe medium was separated by decantation
  3. extractionthe aqueous phase was re-extracted with ethyl acetate
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at atmospheric pressure at 500 ml
  7. distillationThe distillation
  8. customis 83° C
  9. extractiona dry extract

Sources & evidence

ORD record
ord-b2f3223b90bb45329aef40a43c494928
Source dataset
uspto-grants-2012_09
Patent number
US08258328B2

Reaction notes

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