Acetic Acid → (8E,12E,14E)-3,6,21-Tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide

HRID 1446637ノート

反応式

HRID 1446637 の反応式
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH:11]1[C:12]([O:54][CH:55]([O:57][CH2:58][CH3:59])[CH3:56])([CH3:53])[CH2:13][CH2:14][CH:15]([O:47][CH:48]([O:50][CH2:51][CH3:52])[CH3:49])[CH2:16][C:17]([O:19][CH:20](/[C:25](/[CH3:46])=[CH:26]/[CH:27]=[CH:28]/[CH:29]([CH3:45])[CH2:30][CH:31]2[O:44][CH:32]2[CH:33]([CH3:43])[CH:34]([O:37][CH:38]([O:40][CH2:41][CH3:42])[CH3:39])[CH2:35][CH3:36])[CH:21]([CH3:24])[CH:22]=[CH:23]1)=[O:18])(=O)C.C(O)(=O)C.C(OCC)(=O)C>CO.O>[CH2:51]([O:50][CH:48]([O:47][CH:15]1[CH2:14][CH2:13][C:12]([O:54][CH:55]([O:57][CH2:58][CH3:59])[CH3:56])([CH3:53])[CH:11]([OH:10])[CH:23]=[CH:22][CH:21]([CH3:24])[CH:20](/[C:25](/[CH3:46])=[CH:26]/[CH:27]=[CH:28]/[CH:29]([CH3:45])[CH2:30][CH:31]2[O:44][CH:32]2[CH:33]([CH3:43])[CH:34]([O:37][CH:38]([O:40][CH2:41][CH3:42])[CH3:39])[CH2:35][CH3:36])[O:19][C:17](=[O:18])[CH2:16]1)[CH3:49])[CH3:52]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 21024001HCID 21024001、化合物

生成物 1

HCID 21023947(8E,12E,14E)-3,6,21-Tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide収率 102.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Potassium carbonate (138 mg, 0,996 mmol) was added to a solution of (8E,12E,14E)-7-acetoxy-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (250 mg, 0.332 mmol) in methanol (5 mL) at room temperature, followed by stirring at the same temperature for 2 hours. Acetic acid (60 mg, 1 mmol), ethyl acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, spherical, neutral, 40 to 50 μm, ethyl acetate-hexane=1:2 and 1:1, successively) to obtain the title compound (242 mg, 100%) as a colorless oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N

出典と根拠

ORDレコード
ord-bcb1d3ce826a4efaa131b6ff38b3f06e
出典データセット
uspto-grants-2010_02
特許番号
US07667052B2

反応ノート

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