Thionyl Chloride → HCID 44598114, compound

HRID 1408308Notes

Reaction equation

HRID 1408308 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[S:16]([OH:19])(=O)=[O:17])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].S(Cl)([Cl:22])=O>N1C=CC=CC=1>[CH2:1]([O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[S:16]([Cl:22])(=[O:19])=[O:17])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 44598055HCID 44598055, compound

Product 1

HCID 44598114HCID 44598114, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirring solution of sulfonic acid 6a (266 mg, 0.9 mmol) in pyridine (2 mL) was added thionyl chloride (0.2 mL, 2.8 mmol) dropwise. The resulting solution was allowed to stir for 4 h and then the reaction mixture concentrated in vacuo. The resulting residue was purified using column chromatography (5:1 hexanes:EtOAc) to give 7a (140 mg, 50%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.63-1.70 (m, 2H), 1.87-1.93 (m, 2H), 2.10-2.16 (m, 2H), 3.88 (s, 3H), 4.14 (t, J=6.2 Hz, 2H), 4.95-5.05 (m, 2H), 5.76-5.86 (m, 1H), 6.51-6.54 (m, 3H), 7.84 (d, J=9.6 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 24.9, 28.1, 33.1, 55.9, 69.2, 99.9, 104.6, 114.7, 124.3, 131.7, 138.3, 158.7, 166.8.

Workup

  1. concentrationthe reaction mixture concentrated in vacuo
  2. customThe resulting residue was purified

Sources & evidence

ORD record
ord-689f4e07f8484a7a95ec557c94b35d5d
Source dataset
uspto-grants-2014_12
Patent number
US08921349B2

Reaction notes

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