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

HRID 275682

Reaction equation

HRID 275682 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-1b63e531ec1942c3a50d37705d882e6b
Source dataset
uspto-grants-2002_03
Patent number
US06352980B1

Linked notes

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