Potassium Carbonate → 2-n-Butyl-3-[4-(2,3-epoxypropoxy)phenylsulfonyl]benzofuran

HRID 1764663Notes

Reaction equation

HRID 1764663 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=2[C:9]=1[S:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[CH2:30]([CH:32]1[O:34][CH2:33]1)Br>CC(C)=O>[CH2:1]([C:5]1[O:6][C:7]2[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=2[C:9]=1[S:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:30][CH:32]2[O:34][CH2:33]2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 149563642-n-Butyl-3-(4-hydroxyphenylsulfonyl)benzofuran

Product 1

HCID 227688372-n-Butyl-3-[4-(2,3-epoxypropoxy)phenylsulfonyl]benzofuran

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-n-Butyl-3-(4-hydroxyphenylsulfonyl)benzofuran (1.5 g., 0.0045 mol.) was dissolved in 40 ml. of dry acetone containing 2.5 g. (0.018 mol.) of potassium carbonate and 2.46 g. (0.018 mol.) of epibromohydrin. The mixture was refluxed for ca. 16 hours then filtered. The solvent and excess epibromohydrin were removed in vacuo to give 2-n-butyl-3-[4-(2,3-epoxypropoxy)phenylsulfonyl]benzofuran.

Workup

  1. temperatureThe mixture was refluxed for ca. 16 hours
  2. filtrationthen filtered
  3. customThe solvent and excess epibromohydrin were removed in vacuo

Sources & evidence

ORD record
ord-5b7709ca6bb14565b04340e0e9d48895
Source dataset
uspto-grants-1978_09
Patent number
US04117128

Reaction notes

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