Ethyl 4-chlorobenzoylformate → 5-(4-chlorophenyl)-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanone

HRID 369141Notes

Reaction equation

HRID 369141 reaction equation
[CH3:1][Mg]I.[Cl:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([C:11]([O:13]CC)=O)=[O:10])=[CH:7][CH:6]=1.[OH:18][C:19]1[C:20](=O)[O:21][C:22](C)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)C=1O>C1COCC1>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]2([CH3:1])[O:10][C:19](=[O:18])[C:20]([O:21][CH2:22][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:11]2[OH:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 2758815Ethyl 4-chlorobenzoylformateHCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanoneHCID 178418373HCID 178418373, compound

Product 1

HCID 547235885-(4-chlorophenyl)-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanoneYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 3.4 mL (10.2 mmol) of 3.0M methylmagnesium iodide was added to a solution of 2.34 g (10 mmol) of ethyl 4-chlorobenzoylformate in THF in an analogous manner as described for the synthesis of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to give prior to hydrogenolysis 1.3 g (40% yield) of 5-(4-chlorophenyl)-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanone as a yellow oil: 1H NMR (CDCl3) δ 7.37-7.21 (m, 9H), 5.10 (s, 2H), 1.73 (s, 3H).

Workup

  1. customto give

Sources & evidence

ORD record
ord-903f642c89ce4f478ed87e75d6029ff4
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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