Benzofuran → HCID 10680421, compound

HRID 591027Notes

Reaction equation

HRID 591027 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[O:3].[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH:10]=[CH:9]1.[O-]S(C(F)(F)F)(=O)=O.C([Yb+2])C.[O-]S(C(F)(F)F)(=O)=O>ClCCl.C1(C)C=CC=CC=1>[O:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([CH:2]([OH:3])[C:1]([O:5][CH2:6][CH3:7])=[O:4])=[CH:9]1

Participants

6

Reactant 3

HCID 9223BenzofuranHCID 70211Ethyl oxoacetate2×HCID 178461636HCID 178461636, compound

Product 1

HCID 10680421HCID 10680421, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Ethyl glyoxylate 50% in toluene (3.72 mL, 18.6 mmol) was added to a solution of benzofuran (2.0 g, 16.9 mmol) and ethyl ytterbium (III) triflate (0.53 g, 0.8 mmol) in dichloromethane (15 mL). The reaction mixture was stirred at room temperature for 48 hours with two additions of an equivalent of ethyl glyoxylate 50% in toluene each day. The reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane/ethyl acetate 95/05 to 80/20) to provide the desired hydroxyl-ester (20a) (1.15 g, 5.2 mmol, 31%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography (cyclohexane/ethyl acetate 95/05 to 80/20)

Sources & evidence

ORD record
ord-1106ebcaa83344c082bb99d27bd221ac
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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