Hydrochloric Acid → HCID 53739123, compound

HRID 971936Notes

Reaction equation

HRID 971936 reaction equation
[C:1]([CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH2:10][C:11]1(C(OC)=O)[C@H:15](/[CH:16]=[CH:17]/[CH:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][C@H:13](C(OC)=O)[C:12]1=[O:29])([O:3]C)=[O:2].[OH-].[Na+].Cl>O.CO.[Cl-].[Na+]>[OH:24][CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:17]=[CH:16][C@H:15]1[CH2:14][CH2:13][C:12](=[O:29])[C@H:11]1[CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH2:5][C:1]([OH:3])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86734461HCID 86734461, compound

Product 1

HCID 53739123HCID 53739123, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 5234Sodium ChlorideSolvent

Procedure

The cyclopentanonetriester of formula IV, dimethyl cis,trans-3-(6-carbomethoxy-2-hexenyl)-4-(3-hydroxy-1-octenyl)-2-oxo-1,3-cyclopentanedicarboxylate (11.2 g), described in Example 82, 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 2 N HCl, diluted with saturated sodium chloride solution and extracted with ether. The ether extract is dried (Na2SO4) and concentrated to yield the title compound as a mixture of C15 epimers is separated by silica gel chromatography using hexane: chloroform: acetic acid: 10:20:1. The less polar epimer is designated epimer A, nmr (CDCl3) δ 1.05 (t, J=5, 3H), 4.20 (1H), 5.33-5.78 (1H), 6.38 (2H). The more polar epimer is designated epimer B, nmr (CDCl3) δ 1.05 (t, J=5, 3H) 4.18 (1H), 5.30-5.77 (1H), 6.74 (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-4ae3497d75794273ac33e5b375d0109e
Source dataset
uspto-grants-1979_07
Patent number
US04161608

Reaction notes

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