Hydrochloric Acid → HCID 53940607, compound

HRID 372855Notes

Reaction equation

HRID 372855 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][C:12]1(C(OCC)=O)[C@H:16](/[CH:17]=[CH:18]/[C:19]([OH:26])([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:15][C@H:14](C(OCC)=O)[C:13]1=[O:32])([O:3]CC)=[O:2].[OH-].[Na+].Cl>O.CO.[Cl-].[Na+]>[OH:26][C:19]([CH3:25])([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:18]=[CH:17][C@H:16]1[CH2:15][CH2:14][C:13](=[O:32])[C@H:12]1[CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH2:6][C:1]([OH:3])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86734085HCID 86734085, compound

Product 1

HCID 53940607HCID 53940607, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 5234Sodium ChlorideSolvent

Procedure

The cyclopentanonetriester of formula 6, diethyl cis,trans-3-(6-carboethoxy-2-hexenyl)-4-(3-hydroxy-3-methyl-1-octenyl)-2-oxo-1,3-cyclopentanedicarboxylate (11.2 g), described in Example 45, is heated to reflux for 1 hr. in a solution of sodium hydroxide (13.4 g) in 80 ml of water and 110 ml of methanol. The mixture is cooled, adjusted to pH 5 with 2N HCl, diluted with saturated sodium chloride solution and extracted with ether. The ether extract is dried (Na2SO4) and concentrated. Chromatography on silica gel yields the title compound νmaxCHCl3 3580, 1740, 1720 cm-1, nmr (CDCl3) δ 0.88 (t, J = 5, 3H), 1.28 (s, 3H), 5.3-5.75 (m, 4H), 6.3 (2xs, 2H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 1 hr
  3. temperatureThe mixture is cooled
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. dry with materialis dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ef4d18019e4f4bbd83df998e17e433bf
Source dataset
uspto-grants-1978_05
Patent number
US04092427

Reaction notes

Loading…