(3-Hydroxy-3-methyloctyl)(triphenyl)phosphonium iodide → ethyl 2-[(2-{(1R,2S,5R)-2-(acetyloxy)-5-[(1E)-4-hydroxy-4-methyl-1-nonenyl]cyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylate

HRID 1888314ノート

反応式

HRID 1888314 の反応式
[I-].[OH:2][C:3]([CH3:30])([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[C:36]([O:39][C@H:40]1[CH2:44][CH2:43][C@H:42]([CH:45]=O)[C@H:41]1[CH2:47][CH2:48][S:49][C:50]1[S:51][CH:52]=[C:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[N:54]=1)(=[O:38])[CH3:37]>O1CCCC1>[C:36]([O:39][C@H:40]1[CH2:44][CH2:43][C@H:42](/[CH:45]=[CH:5]/[CH2:4][C:3]([OH:2])([CH3:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C@H:41]1[CH2:47][CH2:48][S:49][C:50]1[S:51][CH:52]=[C:53]([C:55]([O:57][CH2:58][CH3:59])=[O:56])[N:54]=1)(=[O:38])[CH3:37]

参加物

5

反応物 3

HCID 86054281(3-Hydroxy-3-methyloctyl)(triphenyl)phosphonium iodideHCID 86634273Ethyl 2-({2-[(1R,2S,5S)-2-(acetyloxy)-5-formylcyclopentyl]ethyl}thio)-1,3-thiazole-4-carboxylateHCID 178418339Butyllithium

生成物 1

HCID 66858309ethyl 2-[(2-{(1R,2S,5R)-2-(acetyloxy)-5-[(1E)-4-hydroxy-4-methyl-1-nonenyl]cyclopentyl}ethyl)thio]-1,3-thiazole-4-carboxylate収率 38.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (3-hydroxy-3-methyloctyl)(triphenyl)phosphonium iodide (800 mg) in anhydrous tetrahydrofuran (9.00 mL) was added n-butyllithium (1.60M in hexane, 1.90 mL) at room temperature and the solution was stirred for 1 Hour. To the solution was added a solution of the compound 49 (349 mg) in anhydrous tetrahydrofuran (6.00 mL) was slowly added at −78° C. and the solution was stirred for 2 Hours. The solution temperature was risen to room temperature. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed water and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1) to give the title compound (178 mg) having the following physical data.

後処理

  1. additionwas slowly added at −78° C.
  2. stirringthe solution was stirred for 2 Hours
  3. customwas risen to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe obtained residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-3e9d421a4a4b4158ab3cce3b0ae3657a
出典データセット
uspto-grants-2013_08
特許番号
US08501793B2

反応ノート

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