2-Chlorobenzenesulfonyl chloride → HCID 57122770, compound

HRID 442900Notes

Reaction equation

HRID 442900 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][CH2:12][CH:13]2[O:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.C(N(CC)C(C)C)(C)C.[Cl:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35](Cl)(=[O:37])=[O:36]>ClCCl>[Cl:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35]([O:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][CH2:12][CH:13]2[O:14][CH2:15][CH2:16][CH2:17][O:18]2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1)(=[O:37])=[O:36]

Participants

5

Reactant 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 54359864HCID 54359864, compound

Product 1

HCID 57122770HCID 57122770, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To all of 2-[3-(3-hydroxy-5-methoxyphenyl)propyl]-1,3-dioxane, as prepared in step d, in dichloromethane (2 mL) containing 500 μL of N,N-diisopropylethylamine was added 166 mg (0.79 mmol) of 2-chlorobenzenesulfonyl chloride. After stirring at ambient temperature for 30 min, 5 mg of N,N-dimethylaminopyridine was added and the reaction mixture was stirred for an additional 30 min. The reaction mixture was quenched with 10% aqueous citric acid, extracted into diethyl ether, dried (MgSO4), concentrated, and purified by flash chromatography (dichloromethane/diethyl ether (100:0 to 95:5)) to give 180 mg (77% yield from 2-[3-(3-hydroxy-5-methoxyphenyl)-3-propenyl]-1,3-dioxane) of the title compound. 1H-NMR (300 MHz, CDCl3) δ 7.84 (dd, 1 H, J 1.5, 8 Hz), 7.53-7.63 (m, 2 H), 7.33-7.39 (m, 1 H), 6.59 (t, 1 H, J =2 Hz), 6.50 (m, 2 H), 4.48 (t, 1 H, J=5 Hz), 4.06-4.11 (m, 2 H), 3.70 (s,3 H), 3.71-3.79(m,2 H), 2.49 (t, 2 H, J=5 Hz), 1.98-2.14 (m, 1 H), 1.25-1.6 (m, 5 H). Mass spectrum (MALDI-TOF, gentisic acid matrix) calcd. for C20H23ClO6S: 449.1 (M+Na). Found: 449.1.

Workup

  1. stirringthe reaction mixture was stirred for an additional 30 min
  2. customThe reaction mixture was quenched with 10% aqueous citric acid
  3. extractionextracted into diethyl ether
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by flash chromatography (dichloromethane/diethyl ether (100:0 to 95:5))

Sources & evidence

ORD record
ord-7ca9bb0616b54bcbbd44f29bfd4eadce
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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