Water → HCID 68960656, compound

HRID 221191Notes

Reaction equation

HRID 221191 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:4]12[CH3:5])[C:17]1[CH2:16][CH2:15][C:14](OC)([O:21]C)[CH2:13][C:12]=1[CH2:11][CH2:10]3)#[N:2].O.Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl.C(O)(C)(C)C>[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]2[C@H:9]3[C@H:18]([CH2:19][CH2:20][C@:4]12[CH3:5])[C:17]1[CH2:16][CH2:15][C:14](=[O:21])[CH2:13][C:12]=1[CH2:11][CH2:10]3)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 68958117HCID 68958117, compound

Product 1

HCID 68960656HCID 68960656, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

3 g of 17β-cyano-3,3-dimethoxyestr-5(10)-ene are suspended in a mixture of 24 ml of dichloromethane and 70 ml of t-butanol. After addition of 28 ml of water and 0.11 ml of 60% perchloric acid, the batch is stirred until fully reacted, admixed with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic phase is washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered and the filtrate is evaporated to dryness to leave 17β-cyanoestr-5(10)-en-3-one which is further processed without purification.

Workup

  1. customuntil fully reacted
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-b48e815d48ae4778af86e57568956cff
Source dataset
uspto-grants-2012_06
Patent number
US08207150B2

Reaction notes

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