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tert-Butyl methyl ether → HCID 86670385、化合物

HRID 1972529
ノート
印刷プレビュー

反応式

HRID 1972529 の反応式
[C:1]1([S:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].Br[C:23]1[CH:28]=[CH:27][C:26]([C:29]([OH:38])([C:34]([F:37])([F:36])[F:35])[C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1.COC(C)(C)C>C1(C)C=CC=CC=1>[F:31][C:30]([F:32])([F:33])[C:29]([C:26]1[CH:25]=[CH:24][C:23]([N:13]2[CH2:12][CH2:11][CH:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH2:15][CH2:14]2)=[CH:28][CH:27]=1)([OH:38])[C:34]([F:35])([F:37])[F:36]
参加物反応条件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 15413tert-Butyl methyl etherHCID 5190868HCID 5190868、化合物HCID 232335702-(4-Bromophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 23676156Sodium t-butoxide

生成物 1

HCID 86670385HCID 86670385、化合物収率 89.1%

試薬・触媒・溶媒 1

HCID 1140
Toluene
溶媒

反応条件

温度
100 °C

実験手順

A 15-mL reaction vial was charged with 4-(phenylsulfonyl)piperidine (1.05 g, 4.66 mmol, BetaPharma, Brandford, Conn.), sodium t-butoxide (0.98 g, 10.24 mmol), 2-(4-bromophenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (1.50 g, 4.66 mmol, Bioorg. Med. Chem. Lett. 2002, 12, 3009), chloro(2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(II), methyl-t-butylether adduct (RuPhos Palladacycle) (0.170 g, 0.233 mmol, Strem Chemicals, Inc, Newburyport, Mass.), and toluene (10 mL). The vial was closed and purged with nitrogen for several minutes. The reaction mixture was heated at 100° C. for 2.5 h and allowed to cool to room temperature. The reaction mixture was diluted with water (5 mL) and extracted with EtOAc (10 mL). The organic extract was washed with water (5 mL) and dried over Na2SO4. The solution was filtered and concentrated and then absorbed onto a plug of silica gel and purified by column chromatography (40 g of silica gel, 10 to 30% EtOAc in hexanes) to provide 1,1,1,3,3,3-hexafluoro-2-(4-(4-(phenylsulfonyl)piperidin-1-yl)phenyl)-2-propanol (1.94 g) as white solid

後処理

  1. customA 15-mL reaction
  2. customThe vial was closed
  3. custompurged with nitrogen for several minutes
  4. temperatureto cool to room temperature
  5. additionThe reaction mixture was diluted with water (5 mL)
  6. extractionextracted with EtOAc (10 mL)
  7. extractionThe organic extract
  8. washwas washed with water (5 mL)
  9. dry with materialdried over Na2SO4
  10. filtrationThe solution was filtered
  11. concentrationconcentrated
  12. customabsorbed onto a plug of silica gel
  13. custompurified by column chromatography (40 g of silica gel, 10 to 30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-f30c314bfadb4c6d80ea8fae71208128
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431563B2

反応ノート

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