Sodium Hydroxide → Ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}hepta-2,4,6-trienoate

HRID 442437Notes

Reaction equation

HRID 442437 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[CH:7][CH:8]=[CH:9][CH2:10]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[OH-].[Na+].[Br-].C(OC(C=CC=CC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)C.[O:62]1[CH2:67][CH2:66][CH2:65][CH2:64][CH:63]1[O:68][CH:69]1[CH:73]([O:74][CH:75]2[CH2:80][CH2:79][CH2:78][CH2:77][O:76]2)[CH2:72][CH:71]([CH:81]=O)[CH:70]1[CH2:83][CH2:84][CH:85]([O:91][CH:92]1[CH2:97][CH2:96][CH2:95][CH2:94][O:93]1)[CH2:86][CH2:87][CH2:88][CH2:89][CH3:90]>O.C(Cl)(Cl)Cl>[O:62]1[CH2:67][CH2:66][CH2:65][CH2:64][CH:63]1[O:68][CH:69]1[CH:73]([O:74][CH:75]2[CH2:80][CH2:79][CH2:78][CH2:77][O:76]2)[CH2:72][CH:71]([CH:81]=[CH:10][CH:9]=[CH:8][CH:7]=[CH:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:70]1[CH2:83][CH2:84][CH:85]([O:91][CH:92]1[CH2:97][CH2:96][CH2:95][CH2:94][O:93]1)[CH2:86][CH2:87][CH2:88][CH2:89][CH3:90]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 544198253,4-Di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbaldehydeHCID 736763405-Ethoxycarbonylpenta-2,4-dienyltriphenylphosphonium bromideHCID 178471456HCID 178471456, compound

Product 1

HCID 53768284Ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentyl}hepta-2,4,6-trienoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 5-ethoxycarbonylpenta-2,4-dienyltriphenylphosphorane [prepared by adding N aqueous sodium hydroxide solution (40 ml.) to a stirred solution of 5-ethoxycarbonylpenta-2,4-dienyltriphenylphosphonium bromide (16.4 g.) in water (1000ml.) at 1°-3° C., extracting with chloroform and concentrating the extract to about 250 ml.] was treated at 2° C. under nitrogen with a solution of 3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbaldehyde (8.5 g.) [prepared as described in (m) above]in chloroform (20 ml.). The solution was allowed to stand at room temperature for 18 hours, the chloroform was removed in vacuo and the residue extracted three times with hot petroleum ether (b.p. 40°-60° C.). The combined petroleum extracts were cooled and filtered to remove precipitated triphenylphosphine oxide. The filtrate was evaporated in vacuo and the residue separated by chromatography on silica gel. Elution with petroleum ether (b.p. 40°-60° C.) gave ethyl 7-{3,4-di(2-tetrahydropyranyloxy)-2-[3 -(2-tetrahydropyranyloxy)octyl]cyclopentyl}-hepta-2,4,6-trienoate (6.4 g.), νmax : 1700 cm-1, 1610 cm-1 (liquid film).

Workup

  1. extractionextracting with chloroform
  2. concentrationconcentrating the
  3. extractionextract to about 250 ml
  4. addition] was treated at 2° C. under nitrogen with a solution of 3,4-di(2-tetrahydropyranyloxy)-2-[3-(2-tetrahydropyranyloxy)octyl]cyclopentane carbaldehyde (8.5 g.) [
  5. customprepared
  6. customthe chloroform was removed in vacuo
  7. extractionthe residue extracted three times with hot petroleum ether (b.p. 40°-60° C.)
  8. temperatureThe combined petroleum extracts were cooled
  9. filtrationfiltered
  10. customto remove
  11. customprecipitated triphenylphosphine oxide
  12. customThe filtrate was evaporated in vacuo
  13. customthe residue separated by chromatography on silica gel
  14. washElution with petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-5a3ea12dcbe14a22b568087758ac3ccb
Source dataset
uspto-grants-1977_08
Patent number
US04045467

Reaction notes

Loading…