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Acetic Anhydride → Acetate

HRID 1283477
Notes
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Reaction equation

HRID 1283477 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 2

HCID 175AcetateHCID 6230Norethindrone

Reagents, catalysts & solvents

1
HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4f3638211e3c4776a14f79af607aac78
Source dataset
uspto-grants-1976_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03975412

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes