Ammonium Chloride → HCID 19918473, compound

HRID 518564Notes

Reaction equation

HRID 518564 reaction equation
[CH3:1][Mg+].[Br-].FC(F)(F)S(O[CH2:10][CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12]1)(=O)=O.[NH4+].[Cl-]>C1COCC1.O>[CH2:10]([CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12]1)[CH3:1]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 196063583,4-dihydro-2H-chromen-2-ylmethyl trifluoromethanesulfonateHCID 178418689HCID 178418689, compound

Product 1

HCID 19918473HCID 19918473, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

MeMgBr (45.6 mL, 137 mmol, 3M in ether) was added to a mixture of the title compound from Step 2 (13.5 g, 45.6 mmol) and CuBr-Me2S (1.61 g, 7.74 mmol) in THF (150 mL) at −5° C. The reactions was stirred at rt for 2 h. It was then poured onto a solution of NH4Cl (55 g, 1.04 mol) in water (200 mL) and extracted with DCM (3×150 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (6.66 g, 90%) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 7.09-7.02 (m, 2H), 6.82-6.78 (m, 2H), 3.93-3.87 (m, 1H), 2.84-2.72 (m, 2H), 2.02-1.96 (m, 1H), 1.81-1.61 (m, 3H), 1.04 (t, J=7.2 Hz, 3H).

Workup

  1. extractionextracted with DCM (3×150 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a124f390a8fc4680894a28c4c59dba95
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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