Pyridine → HCID 18595681, compound

HRID 1581064Notes

Reaction equation

HRID 1581064 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].N1C=CC=CC=1.[C:14]([O:17][C:18]1[CH:35]=[CH:34][C:33]2[C@@H:32]3[C@H:23]([C@H:24]4[C@@:28]([CH2:30][CH2:31]3)([CH3:29])[C:27](=[O:36])[CH2:26][CH2:25]4)[CH2:22][C@@H:21]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:20]=2[CH:19]=1)(=[O:16])[CH3:15].C(OC(C)=C)(=O)C>C(Cl)Cl>[C:14]([O:17][C:18]1[CH:35]=[CH:34][C:33]2[C@@H:32]3[C@H:23]([C@H:24]4[C@@:28]([CH2:30][CH2:31]3)([CH3:29])[C:27]([O:36][C:1](=[O:3])[CH3:2])=[CH:26][CH2:25]4)[CH2:22][C@@H:21]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:20]=2[CH:19]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7916Isopropenyl acetateHCID 7918Acetic AnhydrideHCID 68129543HCID 68129543, compound

Product 1

HCID 18595681HCID 18595681, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10.0 g. of 3-hydroxy-6β-ethoxycarbonylmethyl-1,3,5(10)-estratrien-17-one -- produced in accordance with A2 -- is acetylated with 20 ml. of acetic anhydride in 20 ml. of pyridine for 20 hours at room temperature. After precipitation into ice water, filtration, and taking up the precipitate in methylene chloride, the reaction product is dried and evaporated, thus obtaining 11.8 g. of 3-acetoxy-6β-ethoxycarbonylmethyl-1,3,5(10) estratrien-17-one, which is heated to the boiling point with 140 ml. of isopropenyl acetate in the presence of 1.4 g. of p-toluenesulfonic acid and then subjected to a slow distillation. The cooled reaction product is diluted with methylene chloride and washed with sodium bicarbonate solution and water, dried, and evaporated, thus resulting in 13.3 g. of a crude product. After chromatography on silica gel, pure 3,17-diacetoxy-6β-ethoxycarbonylmethyl-1,3,5(10),16-estratetraene is obtained as an almost colorless oil.

Workup

  1. customAfter precipitation
  2. filtrationinto ice water, filtration
  3. customthe reaction product is dried
  4. customevaporated
  5. customthus obtaining 11.8 g
  6. distillationof p-toluenesulfonic acid and then subjected to a slow distillation
  7. customThe cooled reaction product
  8. washwashed with sodium bicarbonate solution and water
  9. customdried
  10. customevaporated
  11. customthus resulting in 13.3 g

Sources & evidence

ORD record
ord-284c0248d4a649c890a5ae785317f6c9
Source dataset
uspto-grants-1976_01
Patent number
US03935245

Reaction notes

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