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Potassium Phosphate, Tribasic → Methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate

HRID 591506
ノート
印刷プレビュー

反応式

HRID 591506 の反応式
[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]1[C:9]2[C:10](OS(C(F)(F)F)(=O)=O)=[CH:11][C:12]([O:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:13][C:8]=2[S:7][CH:6]=1.[CH:34]1(B(O)O)[CH2:36][CH2:35]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].O.CN(C=O)C>[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]1[C:9]2[C:10]([CH:34]3[CH2:36][CH2:35]3)=[CH:11][C:12]([O:14][Si:15]([CH:22]([CH3:23])[CH3:24])([CH:19]([CH3:20])[CH3:21])[CH:16]([CH3:18])[CH3:17])=[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

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 131734520Methyl(4-(((trifluoromethyl)sulfonyl)oxy)-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate

生成物 1

HCID 131734522Methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate収率 91.4%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of methyl(4-(((trifluoromethyl)sulfonyl)oxy)-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate (512 mg) and DMF (10 mL) were added cyclopropylboronic acid (167 mg), potassium phosphate (1238 mg), Pd(OAc)2 (21.83 mg) and tricyclohexylphosphine (82 mg) at room temperature, and the mixture was refluxed for 16 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (372 mg).

後処理

  1. temperaturethe mixture was refluxed for 16 h
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed successively with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

出典と根拠

ORDレコード
ord-7dff6fd2eecb4fe98a755433b3f20f07
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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