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

HRID 442437ノート

反応式

HRID 442437 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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.)

出典と根拠

ORDレコード
ord-5a3ea12dcbe14a22b568087758ac3ccb
出典データセット
uspto-grants-1977_08
特許番号
US04045467

反応ノート

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