1,3-Dibromobenzene → 4-(3-Bromophenyl)-tetrahydro-2H-pyran-4-ol

HRID 2060761ノート

反応式

HRID 2060761 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.C([Li])CCC.CCCCCC.[O:20]1[CH:25]=[CH:24][C:23](=[O:26])[CH:22]=[CH:21]1>C1COCC1>[Br:8][C:4]1[CH:3]=[C:2]([C:23]2([OH:26])[CH2:24][CH2:25][O:20][CH2:21][CH2:22]2)[CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 79271,3-DibromobenzeneHCID 79684H-pyran-4-oneHCID 8058HexaneHCID 178418339Butyllithium

生成物 1

HCID 189962824-(3-Bromophenyl)-tetrahydro-2H-pyran-4-ol収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred −78° C. solution of 1,3-dibromobenzene (19.71 g, 81.05 mmol) in THF (150 mL) is added 1.6 M butyl lithium in hexane (50.66 mL, 81.05 mmol) and the reaction is stirred 10 minutes. 4H-Pyran-4-one, tetrahydro- (5.41 g, 54.04 mmol) is added dropwise and the reaction is stirred at −78° C. for 2 h. The reaction is quenched by addition of saturated aqueous ammonium chloride (25 mL) and is then diluted with minimal water and extracted with EtOAc. The organic layer is dried over Na2SO4 and the solvent is removed under reduced pressure to afford a residue that is purified by silica gel chromatography eluting with a linear gradient of 5% to 100% EtOAc in hexanes to give the title compound (11.18 g, 76%). GC-MS (m/e): (79Br/81Br) 256, 258 (M−1).

後処理

  1. stirringthe reaction is stirred at −78° C. for 2 h
  2. customThe reaction is quenched by addition of saturated aqueous ammonium chloride (25 mL)
  3. additionis then diluted with minimal water
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer is dried over Na2SO4
  6. customthe solvent is removed under reduced pressure
  7. customto afford a residue that
  8. customis purified by silica gel chromatography
  9. washeluting with a linear gradient of 5% to 100% EtOAc in hexanes

出典と根拠

ORDレコード
ord-ccddfd7d55b64b2e9e7c17975147f7ed
出典データセット
uspto-grants-2012_10
特許番号
US08278441B2

反応ノート

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