Hydrochloric Acid → HCID 18790140, compound

HRID 1107119Notes

Reaction equation

HRID 1107119 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([S:13]([CH2:16][C:17]([O:19][CH3:20])=[O:18])(=[O:15])=[O:14])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].Br[CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([S:13]([CH:16]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:17]([O:19][CH3:20])=[O:18])(=[O:14])=[O:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2596681-Bromo-4-phenylbutaneHCID 53337669HCID 53337669, compound

Product 1

HCID 18790140HCID 18790140, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% NaH (0.23 g, 5.84 mmol) in anhydrous DMF (15 mL) is added a solution of methyl (3,4-dimethoxyphenylsulfonyl)acetate in 20 mL of DMF (1.6 g, 5.84 mmol) dropwise over 10 minutes. The mixture is stirred at room temperature for 20 minutes. 1-Bromo-4-phenylbutane (1.6 g, 5.84 mmol) is added and the mixture is stirred at room temperature for 24 hours. The mixture is added to 5% HCl and is extracted with ether. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo and the residue is chromatographed on silica gel (7:3 hexane:ethyl acetate) to afford methyl 2-[(3,4-dimethoxyphenyl)sulfonyl]-6-phenylhexanoate (1.3 g, 55%): 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.30-1.42 (m, 2H), 1.52-1.68 (m, 2H), 1.95-2.12 (m, 2H), 2.48-2.68 (m, 2H), 3.64 (s, 3H). 3.92 (d, 7H), 6.95 (d, 1H), 7.07-7.18 (m, 2H). 7.20-7.30 (m. 4H), 7.44 (d, 1H); MS (EI) m/e 406 (M+).

Workup

  1. stirringthe mixture is stirred at room temperature for 24 hours
  2. extractionis extracted with ether
  3. washThe organic layer is washed with water
  4. dry with materialis dried over MgSO4
  5. customThe solvent is removed in vacuo
  6. customthe residue is chromatographed on silica gel (7:3 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-28b99c6504e84eea9c4e4881f257dbc9
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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