Water → 7-(2-Oxo-5-(3-oxooct-1-enyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid

HRID 442444노트

반응식

HRID 442444 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:13]([CH:14]=[CH:15][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:12][CH:11]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH:10]1[OH:30].S(=O)(=O)(O)[OH:32].C(OCC)C.O>CN(C)C=O.[O-2].[O-2].[O-2].[Cr+6]>[O:30]=[C:10]1[CH:11]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:12][CH:13]([CH:14]=[CH:15][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([OH:32])=[O:1]

참가 물질

7

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 867329952-(7-Hydroxyheptyl)-3-(3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol

생성물 1

HCID 867329967-(2-Oxo-5-(3-oxooct-1-enyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매HCID 6228Dimethylformamide용매2회

실험 절차

Chromium trioxide (4.0 g.) (dried over phosphorus pentoxide) was added portionwise to a stirred solution of 2-(7-hydroxyheptyl)-3-(3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol [2.12 g., prepared as described in Example 2(f)] in dry dimethylformamide (30 ml.), while maintaining the temperature at between 5° and 15° C. A solution of concentrated sulphuric acid (1.4 ml.) in dimethylformamide (40 ml.) was then added and the mixture was stirred at between 5° and 15° C. for a further 90 minutes. Diethyl ether was then added, followed by a minimum quantity of water to produce two readily separable layers. The ethereal layer was separated and stirred with an aqueous 2N sodium carbonate solution. This aqueous layer was then separated, washed with diethyl ether, and then treated with a further quantity of diethyl ether and acidified to pH 4 by the dropwise addition of concentrated hydrochloric acid. The resulting ethereal layer was separated, and the remaining aqueous layer was extracted with a further quantity of diethyl ether. These last two ethereal solutions were then combined, dried over magnesium sulphate, and evaporated to dryness, to give crude 7-(2-oxo-5-(3-oxooct-1-enyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid (1.03 g.), νmax 1720 cm-1, 1700 cm-1, 1670 cm-1, 1625 cm-1, 985 cm-1, which was used as starting material in the following preparation (h) of 7-[2-hydroxy-5-(3-hydroxyoct-1-enyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanoic acid, without further purification being necessary.

후처리

  1. temperaturewhile maintaining the temperature at between 5° and 15° C
  2. customto produce two readily separable layers
  3. customThe ethereal layer was separated
  4. stirringstirred with an aqueous 2N sodium carbonate solution
  5. customThis aqueous layer was then separated
  6. washwashed with diethyl ether
  7. additiontreated with a further quantity of diethyl ether
  8. additionacidified to pH 4 by the dropwise addition of concentrated hydrochloric acid
  9. customThe resulting ethereal layer was separated
  10. extractionthe remaining aqueous layer was extracted with a further quantity of diethyl ether
  11. dry with materialdried over magnesium sulphate
  12. customevaporated to dryness

출처 및 근거

ORD 기록
ord-0cb30b299c904278b1dc8c2bef488317
출처 데이터셋
uspto-grants-1977_08
특허 번호
US04045467

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