Benzoyl chloride → HCID 21024031、化合物

HRID 1795692ノート

反応式

HRID 1795692 の反応式
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:11]([O:13][CH:14]([O:16][CH:17]1[CH2:29][CH2:28][C:27]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])([CH3:30])[CH:26]([OH:37])[CH:25]=[CH:24][CH:23]([CH3:38])[CH:22](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[O:21][C:19](=[O:20])[CH2:18]1)[CH3:15])[CH3:12].[C:61](Cl)(=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1.C(OCC)(=O)C>O1CCCC1.O>[C:61]([O:37][CH:26]1[C:27]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])([CH3:30])[CH2:28][CH2:29][CH:17]([O:16][CH:14]([O:13][CH2:11][CH3:12])[CH3:15])[CH2:18][C:19]([O:21][CH:22](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[CH:23]([CH3:38])[CH:24]=[CH:25]1)=[O:20])(=[O:68])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

参加物

7

反応物 4

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 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

生成物 1

HCID 21024031HCID 21024031、化合物収率 54%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

LiHMDS (1.0 M tetrahydrofuran solution, 81 μL, 81 μmol) was added dropwise to a solution of (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 (10 mg, 14 μmol) in tetrahydrofuran (1 mL) at −40° C. under nitrogen atmosphere. After stirring at the same temperature for 15 min., a solution of benzoyl chloride (17.8 mg, 125 μmol) in tetrahydrofuran (0.4 mL) was added dropwise thereto and the mixture was stirred at 0° C. for 7 hours. Ethyl Acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:4) to obtain the title compound (6.1 mg, 54%) as a colorless oil.

後処理

  1. stirringthe mixture was stirred at 0° C. for 7 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:4)

出典と根拠

ORDレコード
ord-2ee86c3d1f2c40efaeefd80291f29e8a
出典データセット
uspto-grants-2006_04
特許番号
US07026352B1

反応ノート

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