Triethylamine → HCID 53439675, compound

HRID 642253Notes

Reaction equation

HRID 642253 reaction equation
[CH3:1][C:2]([CH3:10])([CH3:9])[CH:3](O)[CH2:4][N+:5]([O-:7])=[O:6].C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[CH3:1][C:2]([CH3:10])([CH3:9])[CH:3]=[CH:4][N+:5]([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13023786HCID 13023786, compound

Product 1

HCID 53439675HCID 53439675, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold mixture of 3,3-dimethyl-1-nitro-butan-2-ol (7.35 g, 50.0 mmol), and triethylamine (17.4 mL, 125 mmol) in dichloromethane (70 mL) at −78° C. was added MsCl (4.64 mL, 60 mmol) dropwise; the mixture was stirred for 2 hours at −78° C. to room temperature. Then solvents were removed, the residue was partitioned between EtOAc and diluted HCl aqueous solution, the EtOAc phase was washed with saturated NaCl aqueous solution, then dried over anhydrous sodium sulfate, filtered, concentrated, to give an oil, the title compound (6.2 g); The title product, 1H NMR (200 MHz, CDCl3): δ (ppm)=7.25 (d, 1H, J=13.4 Hz), 6.88 (d, 1H, J=13.4 Hz), 1.16 (s, 9H).

Workup

  1. customThen solvents were removed
  2. customthe residue was partitioned between EtOAc and diluted HCl aqueous solution
  3. washthe EtOAc phase was washed with saturated NaCl aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil

Sources & evidence

ORD record
ord-1e41ce8926e14258b5b6ed1c9a639d7d
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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