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

HRID 442437노트

반응식

HRID 442437 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

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).

후처리

  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.)

출처 및 근거

ORD 기록
ord-5a3ea12dcbe14a22b568087758ac3ccb
출처 데이터셋
uspto-grants-1977_08
특허 번호
US04045467

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