Benzene → HCID 22800351, compound

HRID 1439802Notes

Reaction equation

HRID 1439802 reaction equation
[OH:1][C@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1.C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:35]1[CH:40]=[CH:39][CH2:38][CH2:37][CH2:36]1>C(OCC)(=O)C>[O:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]1[O:1][C@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 10823960Norprostol, (-)-

Product 1

HCID 22800351HCID 22800351, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.74 parts of methyl 7-(3(S)-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate in 12 parts by volume of dry benzene is added 0.005 part of p-toluenesulfonic acid and 1.74 parts of dihydropyran. The reaction mixture is stirred for 5 minutes under a nitrogen atmosphere and then allowed to stand at room temperature for a further 2 hours. The resulting solution is diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and stripped of solvent under reduced pressure to afford methyl 7-(3(S)-tetrahydropyran-2-yloxy-5-oxocyclopent-1-en-1-yl)-heptanoate.

Workup

  1. waitto stand at room temperature for a further 2 hours
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-b79c9f6c001e4d358abd6c04cfdd9346
Source dataset
uspto-grants-1977_11
Patent number
US04060691

Reaction notes

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