Acetone → HCID 66931861, compound

HRID 270619Notes

Reaction equation

HRID 270619 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) in solution in 0.5 N sodium hydroxide (100 ml) is introduced, over approximately 5 min at around 2° C., into a suspension of 3,3-ethylenedioxyestra-5(10), 9(11)-dien-17-one (MW=314.4; 100 g; 318 mmol) in methanol (1 liter). The mixture is stirred for 2 h at around 2° C. and then acetone (100 ml) is introduced over approximately 15 min at around 5° C. The mixture is stirred for 1 h and the medium is run, at around 20° C., into a stirred mixture of water (2 liters), sodium chloride (500 g) and ethyl acetate (400 ml). The mixture is separated by settling out and the aqueous phase is re-extracted with ethyl acetate. The combined organic phases are washed with water, dried over sodium sulfate and concentrated at normal pressure to 500 ml. The distillation is continued while maintaining the volume constant by gradual introduction of 1,2-dimethoxyethane (DME). The temperature at the end of exchange is 83° C. The solution is used as it is in the subsequent stage, but a dry extract results in the expected product (resin). C20H28O3; MW=316.4:

Workup

  1. stirringThe mixture is stirred for 1 h
  2. customThe mixture is separated
  3. extractionthe aqueous phase is re-extracted with ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at normal pressure to 500 ml
  7. distillationThe distillation
  8. temperaturewhile maintaining the volume constant by gradual introduction of 1,2-dimethoxyethane (DME)
  9. customis 83° C
  10. extractiona dry extract

Sources & evidence

ORD record
ord-dfdaaec6bcf740a796cb532f5b622020
Source dataset
uspto-grants-2008_11
Patent number
US07449572B2

Reaction notes

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