Sodium Chloride → 4-Tetrahydropyranyloxy-2-(6-tetrahydropyranylcarboxyhexyl)cyclopent-2-en-1-one

HRID 1605775Notes

Reaction equation

HRID 1605775 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:16])[CH2:12][CH:13]([OH:15])[CH:14]=1)([OH:3])=[O:2].[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.O.[C:24]1(C)C=[CH:28][C:27](S(O)(=O)=O)=[CH:26][CH:25]=1.C(=O)(O)[O-:36].[Na+].[Cl-].[Na+]>CO.O.CCOCC.C(Cl)Cl>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[O:15][CH:13]1[CH2:12][C:11](=[O:16])[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:1]([OH:3])=[O:2])[CH:28]2[CH2:27][CH2:26][CH2:25][CH2:24][O:36]2)=[CH:14]1

Participants

10

Reactant 5

HCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 3690897ACMC-20apjz

Product 1

HCID 704200994-Tetrahydropyranyloxy-2-(6-tetrahydropyranylcarboxyhexyl)cyclopent-2-en-1-one

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5.59 g. (24.6 mmoles) of 4-hydroxy-2-(6-carboxyhexyl) cylopent-2-en-1-one (Example 122) and 20.7 g. (246 mmoles) of dihydropyran in 100 ml. of methylene chloride at 20°C. is added 47 mg. (0.246 mmoles) of p-toluenesulfonic acid monohydrate in one portion. The temperature is maintained at 20°-25°C. by cooling and is stirred for one hour at that temperature. The solution is diluted with 200 ml. of ether and poured into a mixture of 40 ml. of saturated sodium bicarbonate solution, 40 ml. of saturated sodium chloride solution, and 80 ml. of water. The phases are seaparated, and the aqueous phase is extracted with additional ether. The total extract is washed successively with water and saturated sodium chloride solution, dried over potassium carbonate, and freed of volatile matter by concentration at reduced pressure to give an oil, λ max.MeOH = 223 mμ (9500); ν max. 1730 (ester carbonyl group), 1705 (ketone carbonyl group), and 1030 cm-1 (tetrahydropyranyloxy groups).

Workup

  1. temperatureThe temperature is maintained at 20°-25°C.
  2. temperatureby cooling
  3. additionThe solution is diluted with 200 ml
  4. extractionthe aqueous phase is extracted with additional ether
  5. extractionThe total extract
  6. washis washed successively with water and saturated sodium chloride solution
  7. dry with materialdried over potassium carbonate
  8. concentrationfreed of volatile matter by concentration at reduced pressure
  9. customto give an oil, λ max

Sources & evidence

ORD record
ord-387c50744b5d43f9a90ffc340e6774b8
Source dataset
uspto-grants-1976_04
Patent number
US03950406

Reaction notes

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