Dimethylformamide → Neopentyl 5-methylnaphthalene-2-sulfonate

HRID 234779Notes

Reaction equation

HRID 234779 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 23355541Neopentyl 5-methylnaphthalene-2-sulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-914b0916c0884f21b2c0f287125a116d
Source dataset
uspto-grants-1997_01
Patent number
US05596095

Reaction notes

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