Acetic Anhydride → Acetate

HRID 1283477

Reaktionsgleichung

Reaktionsgleichung von HRID 1283477
[C:1]([O:4]C(=O)C)(=[O:3])[CH3:2].Cl(O)(=O)(=O)=O.[CH3:13][C@:14]12[CH2:22][CH2:21][C@@H:20]3[C:23]4[CH2:24][CH:25]=[C:26]([O:31]C)[CH2:27][C:28]=4[CH2:29][CH2:30][C@H:19]3[C@@H:18]1[CH2:17][CH2:16][C@:15]2([C:34]#[CH:35])[OH:33].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:13][C@:14]12[CH2:22][CH2:21][C@@H:20]3[C@@H:23]4[C:28]([CH2:29][CH2:30][C@H:19]3[C@@H:18]1[CH2:17][CH2:16][C@:15]2([C:34]#[CH:35])[OH:33])=[CH:27][C:26](=[O:31])[CH2:25][CH2:24]4.[C:1]([O-:4])(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 7918Acetic AnhydrideHCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 8673382613-methyl-17alpha-ethynyl-3-methoxygona-2,5(10)-dien-17-Ol

Produkt 2

HCID 175AcetateHCID 6230Norethindrone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Prepare a fresh solution of acetic anhydride (4.8 ml.) and 70% aqueous perchloric acid (0.01 ml.) in ethyl acetate (50 ml.) then add dl-13-methyl-17α-ethynyl-3-methoxygona-2,5(10)-dien- 17-Ol (0.5 g.) as a solid, swirl for 1.5 minutes then quench the reaction by adding saturated aqueous sodium bicarbonate solution. Wash the ethyl acetate layer with saturated bicarbonate, brine and dry over anhydrous sodium sulfate. Filter, evaporate in vacuo then add methanol with a trace of pyridine and let stand for 2 hours. Evaporate in vacuo, pump dry then treat the residue in ether with decolorizing charcoal. Filter, evaporate and crystallize the residue from methanol to obtain dl-13-methyl-17α-ethynyl-17-hydroxygon-4-en-3-one, acetate.

Aufarbeitung

  1. customthen quench
  2. customthe reaction
  3. washWash the ethyl acetate layer with saturated bicarbonate, brine
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationFilter
  6. customevaporate in vacuo
  7. waitadd methanol with a trace of pyridine and let stand for 2 hours
  8. customEvaporate in vacuo
  9. custompump dry
  10. additionthen treat the residue in ether with decolorizing charcoal
  11. filtrationFilter
  12. customevaporate
  13. customcrystallize the residue from methanol

Quellen und Nachweise

ORD-Eintrag
ord-4f3638211e3c4776a14f79af607aac78
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03975412

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