Benzene → HCID 22800352, compound

HRID 1439805Notes

Reaction equation

HRID 1439805 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]([OH:16])=[O:15])=[CH:3]1.[CH:17]1[CH:22]=[CH:21][CH:20]=[CH:19]C=1.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.[O:34]1[CH:39]=[CH:38][CH2:37][CH2:36][CH2:35]1>C(OCC)(=O)C>[O:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH:39]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][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:17][O:30]2)=[O:15])=[CH:3]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 162131497-[(3R)-3-Hydroxy-5-oxocyclopent-1-en-1-yl]heptanoic acid

Product 1

HCID 22800352HCID 22800352, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.70 parts of 7-(3(R)-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoic acid in 12 parts by volume of dry benzene is added 0.005 part of p-toluenesulfonic acid and 3.40 parts of dihydropyran. The reaction mixture is allowed to stand at room temperature for about 24 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 tetrahydropyran-2-yl 7-(3(R)-tetrahydropyran-2-yloxy-5-oxocyclopent-1-en-1-yl)-heptanoate. This compound is represented by the following structural formula. ##STR21##

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-f22df2552fc84a519155c4d63e6b4c1d
Source dataset
uspto-grants-1977_11
Patent number
US04060691

Reaction notes

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