methyl 2-(4-formyl-2-methoxyphenoxy)acetate → HCID 54275296, compound

HRID 428691Notes

Reaction equation

HRID 428691 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][C:7]=1[O:14][CH3:15].[C:17]([Mg]Cl)#[CH:18]>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([OH:13])[C:17]#[CH:18])=[CH:8][C:7]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 882523methyl 2-(4-formyl-2-methoxyphenoxy)acetateHCID 178462451HCID 178462451, compound

Product 1

HCID 54275296HCID 54275296, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[4-(1-Hydroxy-2-propynyl)-2-methoxy-phenoxy]-acetic acid methyl ester was prepared according to Method A above (except the Grignard reagent was added at −78° C.) from (4-formyl-2-methoxy-phenoxy)-acetic acid methyl ester (0.645 g, 2.9 mmol) (from Example 45) in THF (30 mL) and ethynylmagnesium chloride (3.45 mmol, 7 mL, 0.5M solution in tetrahydrofuran) (Aldrich). (Yield 525 mg, 72%).

Sources & evidence

ORD record
ord-af66debbc7e04b48b3bc5dc8a24d76bf
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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