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Tetrahydrofuran → Methyl(4-cyclopropyl-6-hydroxy-1-benzothiophen-3-yl)acetate

HRID 591507
ノート
印刷プレビュー

反応式

HRID 591507 の反応式
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([CH:25]3[CH2:27][CH2:26]3)=[CH:11][C:12]([O:14][Si](C(C)C)(C(C)C)C(C)C)=[CH:13][C:8]=2[S:7][CH:6]=1.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([CH:25]3[CH2:27][CH2:26]3)=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131734522Methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate

生成物 1

HCID 131734523Methyl(4-cyclopropyl-6-hydroxy-1-benzothiophen-3-yl)acetate収率 86.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate (372 mg) and THF (2 mL) was added TBAF (1M in THF, 1.333 mL) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (201 mg).

後処理

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

出典と根拠

ORDレコード
ord-318f2eea7f5b440bb2f7ca5234f14ab0
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238639B2

反応ノート

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