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 1446637노트

반응식

HRID 1446637 반응식
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]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 21024001HCID 21024001, 화합물

생성물 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-olide수율 102.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bcb1d3ce826a4efaa131b6ff38b3f06e
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07667052B2

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