Ethylene Glycol → HCID 69527274, compound

HRID 858328Notes

Reaction equation

HRID 858328 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:29]=[CH:28][C:8]([C:9]([C:11]2[C:15]3[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:19][C:14]=3[O:13][C:12]=2[CH2:24][CH2:25][CH2:26][CH3:27])=[O:10])=[CH:7][CH:6]=1.[CH2:30](O)[CH2:31][OH:32].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]2([C:11]3[C:15]4[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:19][C:14]=4[O:13][C:12]=3[CH2:24][CH2:25][CH2:26][CH3:27])[O:32][CH2:31][CH2:30][O:10]2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 69527588HCID 69527588, compound

Product 1

HCID 69527274HCID 69527274, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.0 g (0.022 mol) of methyl 3-[4-(2-bromoethoxy)benzoyl]-2-butylbenzofuran-5-carboxylate, 3.39 g (0.055 mol) of ethylene glycol, 890 mg of para-toluenesulfonic acid (pTsA) and 100 ml of benzene are brought to reflux for 3 days, eliminating the water formed using a Dean-Stark apparatus. The mixture is evaporated to dryness and the residue is chromatographed on a column of silica, eluting with DCM (dichloromethane) and then a DCM/ethyl acetate (99/1) mixture. 5 g of the pure desired compound are thus isolated.

Workup

  1. temperatureto reflux for 3 days
  2. customformed
  3. customThe mixture is evaporated to dryness
  4. customthe residue is chromatographed on a column of silica
  5. washeluting with DCM (dichloromethane)

Sources & evidence

ORD record
ord-c887bd4755b740e1b423babe537d91b7
Source dataset
uspto-grants-2006_12
Patent number
US07148240B2

Reaction notes

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