Dimethylformamide → Neopentyl 5-methylnaphthalene-2-sulfonate

HRID 234779ノート

反応式

HRID 234779 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([O:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:14])=[O:13])=[CH:7]2.[C:21]([Li])(C)(C)C.CN(C)C=O>CCOCC>[CH3:21][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([O:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:14])=[O:13])=[CH:7]2

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 10948283Neopentyl 5-bromonaphthalene-2-sulfonateHCID 178418306HCID 178418306、化合物

生成物 1

HCID 23355541Neopentyl 5-methylnaphthalene-2-sulfonate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a cooled (-80° C.) solution of neopentyl 5-bromonaphthalene-2-sulfonate (300 mg; 0.84 mmol) in anhydrous ether (12 mL) is added tert-butyllithium (1.7M in ether) (1 mL; 1.7 mmol), immediately followed by a solution of dimethylformamide (125 mg; 1.7 mmol) in ether (2 mL). The external cooling bath is removed and stirring is allowed to proceed for 1 hour. The reaction mixture is quenched with water (10 mL), the two solution phases are separated and the aqueous phase is extracted with ether (2×10 mL). The combined organic phase is dried (MgSO4), filtered and concentrated under reduced pressure to afford crude neopentyl 5-methylnaphthalene-2-sulfonate.

後処理

  1. customThe external cooling bath is removed
  2. customThe reaction mixture is quenched with water (10 mL)
  3. customthe two solution phases are separated
  4. extractionthe aqueous phase is extracted with ether (2×10 mL)
  5. dry with materialThe combined organic phase is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-914b0916c0884f21b2c0f287125a116d
出典データセット
uspto-grants-1997_01
特許番号
US05596095

反応ノート

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