Methyl Methanesulfonate → Methyl (1-hydroxy-4-methyl-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate

HRID 1798320ノート

反応式

HRID 1798320 の反応式
[CH3:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3].[Li]CCCC.[CH3:12][C:13]1[CH:20]=[C:19]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:18]=[C:17]([B:28]2[O:32]C(C)(C)[C:30](C)(C)[O:29]2)[C:14]=1C=O>C1COCC1>[OH:32][B:28]1[C:17]2[CH:18]=[C:19]([O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[CH:20]=[C:13]([CH3:12])[C:14]=2[CH:30]([CH2:1][S:2]([O:5][CH3:6])(=[O:4])=[O:3])[O:29]1

参加物

5

反応物 3

HCID 4156Methyl MethanesulfonateHCID 582927792-Methyl-4-((tetrahydro-2H-pyran-2-yl)oxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 58292744Methyl (1-hydroxy-4-methyl-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a cooled (−78° C.) solution of methyl methanesulfonate (1.56 mL, 20 mmol) in 15 ml anhydrous THF was added 1.6 M n-BuLi in hexanes (11.25 ml, 18 mmol) dropwise. The mixture was stirred at −78° C. for 20 minutes, then a solution of 2-methyl-4-(tetrahydro-2H-pyran-2-yloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (2.07 g, 6 mmol) in 15 mL THF was added slowly via syringe. After stirring at −78° C. for 10 minutes, the reaction was quenched with saturated ammonium chloride at −78° C. It was then extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give crude product, which was purified by flash column. (1.64 g) MS (ESI) m/z=713 [2M+H]+.

後処理

  1. stirringAfter stirring at −78° C. for 10 minutes
  2. customthe reaction was quenched with saturated ammonium chloride at −78° C
  3. extractionIt was then extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto give crude product, which
  8. customwas purified by flash column

出典と根拠

ORDレコード
ord-708cc1ee55eb4c0aa4104551103cf5b1
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

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