Sodium Chloride → Methyl 7-{(3R)-3-[(oxan-2-yl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoate

HRID 436917Notes

Reaction equation

HRID 436917 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:12](=[O:17])[CH2:13][C@@H:14]([OH:16])[CH:15]=1)([O:3][CH3:4])=[O:2].[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>O.C(Cl)Cl>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:16][C@@H:14]1[CH2:13][C:12](=[O:17])[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:1]([O:3][CH3:4])=[O:2])=[CH:15]1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 10800078METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE

Product 1

HCID 13216834Methyl 7-{(3R)-3-[(oxan-2-yl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A vigorously stirred, ice-cold solution of 10 g. of 2-(6-carbomethoxyhexyl)-4(R)-hydroxy-cyclopent-2-en-1-one [R. Pappo, et al., Tetrahedron Letters, 943(1973)] and 15 g. of dihydropyran in 215 ml. of methylene chloride is treated with 85 mg. of p-toluenesulfonic acid monohydrate. After stirring for 5 minutes at 0° C. and 60 minutes at 25° C., the solution is poured into a stirred mixture of 40 ml. of saturated sodium chloride solution, 40 ml. of saturated sodium bicarbonate solution and 80 ml. of water. The organic phase is washed with brine, dried over magnesium sulfate, and concentrated to give an oil, λmax (film) 1730 (ester carbonyl), 1710 (ketone carbonyl), and 1030 cm-1 (tetrahydropyranyloxy group).

Workup

  1. stirringAfter stirring for 5 minutes at 0° C. and 60 minutes at 25° C.
  2. additionthe solution is poured into a stirred mixture of 40 ml
  3. washThe organic phase is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give an oil, λmax (film) 1730 (ester carbonyl), 1710 (ketone carbonyl), and 1030 cm-1 (tetrahydropyranyloxy group)

Sources & evidence

ORD record
ord-7ad0c72464f045fbb16281dcb0caf544
Source dataset
uspto-grants-1977_06
Patent number
US04028396

Reaction notes

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