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

HRID 261914ノート

反応式

HRID 261914 の反応式
[OH:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1.[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>CCOCC.CO.C(Cl)Cl>[O:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]1[O:1][CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3]1

参加物

9

反応物 5

HCID 5234Sodium ChlorideHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 98379417-(3-Hydroxy-5-oxo-1-cyclopentenyl)-heptanoic acid ethyl ester

生成物 1

HCID 131895154-Tetrahydropyranyloxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one

試薬・触媒・溶媒 3

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

実験手順

To a stirred solution of 674 mg. (2.64 mmoles) of 4-hydroxy-2-(6-carbethoxyhexyl)cyclopent-2-en-1-one (Example 29) and 2.22 g. (26.4 mmoles) of dihydropyran in 2.6 ml. of methylene chloride is added 5.0 mg. (0.026 mmoles) of p-toluenesulfonic acid monohydrate. After stirring for 20 minutes at room temperature the solution is diluted with ether and poured into saturated sodium chloride solution containing a little sodium bicarbonate. The organic phase is separated and washed with saturated sodium chloride solution. The extract is dried over magnesium sulfate, and volatile matter is evaporated at reduced pressure to give an oil, λmax.MeOH =224 mμ (7950); νmax.=1735 (ester carbonyl group), 1710 (ketone carbonyl group), and 1030 cm-1 (tetrahydropyranyloxy group).

後処理

  1. customThe organic phase is separated
  2. washwashed with saturated sodium chloride solution
  3. dry with materialThe extract is dried over magnesium sulfate, and volatile matter
  4. customis evaporated at reduced pressure
  5. customto give an oil, λmax

出典と根拠

ORDレコード
ord-bf458724f4544bb2a3303bef3b40bf02
出典データセット
uspto-grants-1979_05
特許番号
US04152524

反応ノート

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