HCID 18594629, compound → HCID 18594628, compound

HRID 328518Notes

Reaction equation

HRID 328518 reaction equation
[CH2:1]1[CH2:28][O:27][C:3]2([CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][C@@H:20]([OH:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[O:2]1>C(Cl)Cl>[CH2:28]1[CH2:1][O:2][C:3]2([CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C@H:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[O:27]1

Participants

3

Reactant 1

HCID 18594629HCID 18594629, compound

Product 1

HCID 18594628HCID 18594628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 14.5 g. of chromium trioxide-pyridine complex in 110 ml. of dry methylene chloride is added with stirring 4.82 g. of 1-methyl 9,9-(ethylenedioxy)-15(S)-hydroxy-prostanoate (Example 134) in 17 ml. of methylene chloride. The resulting dark brown mixture is stirred at ambient temperature for 18 hours. The mixture is filtered and the mother liquor is taken to dryness. The residue is taken up in ether and washed successively with ice cold 5% sodium hydroxide, saturated sodium chloride solution, 30% sodium phosphate monobasic solution and water dried with anhydrous sodium sulfate and evaporated to dryness under reduced pressure to afford 4.17 g. (98%) of product as an oil; λ max 5.71, 5.82μ (carbonyl groups).

Workup

  1. additionTo a mixture of 14.5 g
  2. stirringThe resulting dark brown mixture is stirred at ambient temperature for 18 hours
  3. filtrationThe mixture is filtered
  4. washwashed successively with ice cold 5% sodium hydroxide, saturated sodium chloride solution, 30% sodium phosphate monobasic solution and water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customto afford 4.17 g

Sources & evidence

ORD record
ord-8f7288aaa52345749cd530ce0b93a84f
Source dataset
uspto-grants-1977_04
Patent number
US04017534

Reaction notes

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