Pyridine → Estra-1,3,5,7,9,16-hexaen-3-YL acetate

HRID 1108460Notes

Reaction equation

HRID 1108460 reaction equation
[CH3:1][C@:2]12[CH2:18][CH2:17][C:16]3[C:15]4[CH:14]=[CH:13][C:12]([OH:19])=[CH:11][C:10]=4[CH:9]=[CH:8][C:7]=3[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:16]3[CH2:17][CH2:18][C@@:2]4([CH3:1])[C@@H:6]([CH2:5][CH:4]=[CH:3]4)[C:7]=3[CH:8]=[CH:9][C:10]=2[CH:11]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54020244Estra-1,3,5(10),6,8,16-hexaen-3-ol

Product 1

HCID 68408994Estra-1,3,5,7,9,16-hexaen-3-YL acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of estra-1,3,5(10),6,8,16-hexaen-3-ol Q8, 148.8 mg, 0.5944 mmol) in anh. pyridine (2.0 ml, 25 mmol) and acetic anhydride (0.28 ml, 3.0 mmol) was stirred 6 h, after which ethyl acetate (20 ml) was added. See FIG. 159. 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 sodium sulfate, and filtered. The residue was washed with 5 ml of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Recrystallization from 95% ethanol gave lustrous white platelets (99.4 mg, 0.340 mmol, 55%, m.p. 9596° C. TLC (2% ethyl acetate/hazanes on silica gel) showed product (Rf 0.1) contained a trace contaminant at the origin.

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 sodium sulfate
  3. filtrationfiltered
  4. washThe residue was washed with 5 ml of ethyl acetate
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. customRecrystallization from 95% ethanol
  7. customgave lustrous white platelets (99.4 mg, 0.340 mmol, 55%, m.p. 9596° C

Sources & evidence

ORD record
ord-56a9ec48d2eb4f60a9b9e8a7b55af1f3
Source dataset
uspto-grants-2000_05
Patent number
US06066627

Reaction notes

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