Acetic Anhydride → Acetate

HRID 1283477

반응식

HRID 1283477 반응식
[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]

참가 물질

7

반응물 4

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

생성물 2

HCID 175AcetateHCID 6230Norethindrone

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4f3638211e3c4776a14f79af607aac78
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03975412

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