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Acetic Acid → 2-Methylthio-5-(1-methoxycarbonylhexyl)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone

HRID 1197042
ノート
印刷プレビュー

反応式

HRID 1197042 の反応式
[CH3:1][S:2][C:3]1[C:4](=[O:35])[CH:5]([CH:24](O)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]C(OC)=O)[CH:6]([CH:8]=[CH:9][CH:10]([O:16][Si](C(C)(C)C)(C)C)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1.[C:36]([OH:39])(=[O:38])C.O1CCC[CH2:41]1.O>C1(C)C=CC=CC=1>[CH3:1][S:2][C:3]1[C:4](=[O:35])[CH:5]([CH:24]([C:36]([O:39][CH3:41])=[O:38])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:6]([CH:8]=[CH:9][CH:10]([OH:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 572430522-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone

生成物 1

HCID 571268992-Methylthio-5-(1-methoxycarbonylhexyl)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone収率 65%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

実験手順

To 350 mg of 2-methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone obtained in Example 6 was added a solvent mixture of 10 ml of acetic acid, 5 ml of tetrahydrofuran, and 5 ml of water, and the mixture was stirred for 24 hours. Toluene was then added, and after concentration, the concentrate was diluted with saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. Subsequently, the extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated, followed by silica gel chromatography to give 178 mg (yield 65%) of 2-methylthio-5-(1-methoxycarbonylhexyl)-4-(3-hydroxy-1-octenyl)-2-cyclopentenone.

後処理

  1. concentrationafter concentration
  2. additionthe concentrate was diluted with saturated aqueous sodium hydrogencarbonate
  3. extractionextracted with ethyl acetate
  4. washSubsequently, the extract was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1171379d35ab4c269882b94c1226a591
出典データセット
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05116869

反応ノート

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