Hydrochloric Acid → HCID 57174641, compound

HRID 442901Notes

Reaction equation

HRID 442901 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O:11][C:12]1[CH:13]=[C:14]([CH2:20][CH2:21][CH2:22][CH:23]2OCCC[O:24]2)[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)(=[O:10])=[O:9].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O:11][C:12]1[CH:13]=[C:14]([CH2:20][CH2:21][CH2:22][CH:23]=[O:24])[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)(=[O:9])=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57122770HCID 57122770, compound

Product 1

HCID 57174641HCID 57174641, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 156 mg (0.38 mmol) 2-[3-[3-(2-chlorophenylsulfonyloxy)-5-methoxyphenyl]propyl]-1,3-dioxane, as prepared in the preceding step, in 2 mL of tetrahydrofuran was treated with 4.5 μL of 10% aqueous hydrochloric acid. The reaction mixture was stirred at 60° C. for 1 h. The reaction mixture was diluted with water, extracted into dichloromethane, dried (MgSO4), and purified by flash chromatography (dichloromethane) to give 23.4 mg of the title compound as the minor product of the reaction. 1H-NMR (300 MHz, CDCl3) δ 9.70 (t, 1 H, J=2 Hz), 7.93 (dd, 1 H, J=1.5,8Hz), 7.52-7.9 (m, 2 H), 6.57 (t, 1 H), 6.52 (t, 1 H, J=2 Hz), 6.49 (t, 1 H, J=2 Hz), 3.69 (s, 3 H), 2.52 (t, 2 H, J=7 Hz), 2.33 (dt, 2 H, J=1.5, 7 Hz), 1.80 (pentet, 2 H, J=7 Hz).

Workup

  1. extractionextracted into dichloromethane
  2. dry with materialdried (MgSO4)
  3. custompurified by flash chromatography (dichloromethane)

Sources & evidence

ORD record
ord-1a64f9897e524e6cb5b38217da7815e6
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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