Pyridine → Estra-1,3,5(10),7,16-pentaen-3-yl acetate

HRID 275679Notes

Reaction equation

HRID 275679 reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C:7](=[CH:8][CH2:9][C:10]4[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=43)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(OCC)(=O)C>[C:26]([O:19][C:12]1[CH:13]=[CH:14][C:15]2[C@@H:16]3[C:7]([C@H:6]4[C@@:2]([CH2:18][CH2:17]3)([CH3:1])[CH:3]=[CH:4][CH2:5]4)=[CH:8][CH2:9][C:10]=2[CH:11]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 22873080Estra-1,3,5(10),7,16-pentaen-3-ol

Product 1

HCID 68410585Estra-1,3,5(10),7,16-pentaen-3-yl acetateYield 35.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of estra-1,3,5(10),7,16-pentaen-3-ol (5, 192.1 mg, 0.7612 mmol) in anh. pyridine (2.6 mL, 32 mmol) and acetic anhydride (0.36 mL, 3.8 mmol) was stirred 6 h, after which 30 mL of ethyl acetate were added. The mixture was washed with three 10 mL portions of 1 N hydrochloric acid+10 mL of saturated sodium bicarbonate+10 mL of brine, dried over magnesium sulfate, and filtered through diatomaceous earth. See Example 15. The residue was washed with 10 mL of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Preparative TLC (5% ethyl acetate/hexanes on silica gel GF, 1000μ thickness) and recrystallization from aqueous ethanol gave fine white needles (78.6 mg, 0.267 mmol, 35%), m.p. 77-80° C. TLC (4% ethyl acetate/hexanes on silica gel) showed 2 spots at Rf 0.21 and 0.24.

Workup

  1. washThe mixture was washed with three 10 mL portions of 1 N hydrochloric acid+10 mL of saturated sodium bicarbonate+10 mL of brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered through diatomaceous earth
  4. washThe residue was washed with 10 mL of ethyl acetate
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. customPreparative TLC (5% ethyl acetate/hexanes on silica gel GF, 1000μ thickness) and recrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-37bdca3055494e5bb9f7298ada2d3be2
Source dataset
uspto-grants-2002_03
Patent number
US06352980B1

Reaction notes

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