Sodium Chloride → 4-Tetrahydropyranyloxy-2-(6-tetrahydropyranylcarboxyhexyl)cyclopent-2-en-1-one

HRID 261913

反応式

HRID 261913 の反応式
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:16])[CH2:12][CH:13]([OH:15])[CH:14]=1)([OH:3])=[O:2].[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.O.[C:24]1(C)C=[CH:28][C:27](S(O)(=O)=O)=[CH:26][CH:25]=1.C(=O)(O)[O-:36].[Na+].[Cl-].[Na+]>CO.O.CCOCC.C(Cl)Cl>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[O:15][CH:13]1[CH2:12][C:11](=[O:16])[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:1]([OH:3])=[O:2])[CH:28]2[CH2:27][CH2:26][CH2:25][CH2:24][O:36]2)=[CH:14]1

参加物

10

反応物 5

HCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 3690897ACMC-20apjz

生成物 1

HCID 704200994-Tetrahydropyranyloxy-2-(6-tetrahydropyranylcarboxyhexyl)cyclopent-2-en-1-one

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 5.59 g. (24.6 mmoles) of 4-hydroxy-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 28) and 20.7 g. (246 mmoles) of dihydropyran in 100 ml. of methylene chloride at 20° C. is added 47 mg. (0.246 mmoles) of p-toluenesulfonic acid monohydrate in one portion. The temperature is maintained at 20°-25° C. by cooling and is stirred for one hour at that temperature. The solution is diluted with 200 ml. of ether and poured into a mixture of 40 ml. of saturated sodium bicarbonate solution, 40 ml. of saturated sodium chloride solution, and 80 ml. of water. The phases are separated and the aqueous phase is extracted with additional ether. The total extract is washed successively with water and saturated sodium chloride solution, dried over potassium carbonate, and freed of volatile matter by concentration at reduced pressure to give an oil, λmax.MeOH =223 mμ (9500); νmax. 1730 (ester carbonyl group), 1705 (ketone carbonyl group), and 1030-1 (tetrahydropyranyloxy groups).

後処理

  1. temperatureThe temperature is maintained at 20°-25° C.
  2. temperatureby cooling
  3. additionThe solution is diluted with 200 ml
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with additional ether
  6. extractionThe total extract
  7. washis washed successively with water and saturated sodium chloride solution
  8. dry with materialdried over potassium carbonate
  9. concentrationfreed of volatile matter by concentration at reduced pressure
  10. customto give an oil, λmax

出典と根拠

ORDレコード
ord-23839d36a98e438ba480b450f8b4e1cc
出典データセット
uspto-grants-1979_05
特許番号
US04152524

関連ノート

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