Pyridine → 17-Methylenestra-1,3,5(10)-trien-3-yl acetate

HRID 275682

반응식

HRID 275682 반응식
[CH2:1]=[C:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C:16]1[CH:15]=[CH:14][C:13]([OH:20])=[CH:12][C:11]=1[CH2:10][CH2:9]3.N1C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(OCC)(=O)C>[C:27]([O:20][C:13]1[CH:14]=[CH:15][C:16]2[C@@H:17]3[C@H:8]([C@H:5]4[C@@:3]([CH2:19][CH2:18]3)([CH3:4])[C:2](=[CH2:1])[CH2:7][CH2:6]4)[CH2:9][CH2:10][C:11]=2[CH:12]=1)(=[O:29])[CH3:28]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1445855217-Methylene-estra-1,3,5(10)-trien-3-ol

생성물 1

HCID 1864230517-Methylenestra-1,3,5(10)-trien-3-yl acetate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A solution of 17-methylenestra-1,3,5(10)-trien-3-ol (10, 5.84 g, 21.8 mmol) in anh. pyridine (32 mL, 0.40 mol) and acetic anhydride (9.7 mL, 0.10 mol) was stirred 24, after which ethyl acetate (250 mL) was added. See FIG. 17. The mixture was washed with three 100 mL portions of 1 N hydrochloric acid+100 mL of saturated sodium bicarbonate+100 mL of saturated copper sulfate+100 mL of brine, dried over magnesium sulfate, and filtered through diatomaceous earth. The residue was washed with 25 mL of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Recrystallization from aqueous ethanol gave lustrous white platelets (5.84 g, 18.8 mmol), m.p. 77-79° C.

후처리

  1. washThe mixture was washed with three 100 mL portions of 1 N hydrochloric acid+100 mL of saturated sodium bicarbonate+100 mL of saturated copper sulfate+100 mL of brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered through diatomaceous earth
  4. washThe residue was washed with 25 mL of ethyl acetate
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. customRecrystallization from aqueous ethanol
  7. customgave lustrous white platelets (5.84 g, 18.8 mmol), m.p. 77-79° C.

출처 및 근거

ORD 기록
ord-1b63e531ec1942c3a50d37705d882e6b
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06352980B1

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