Dimethylformamide → Neopentyl 5-methylnaphthalene-2-sulfonate

HRID 234779노트

반응식

HRID 234779 반응식
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

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 10948283Neopentyl 5-bromonaphthalene-2-sulfonateHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 23355541Neopentyl 5-methylnaphthalene-2-sulfonate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-914b0916c0884f21b2c0f287125a116d
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05596095

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