Ethyl vanillate → Ethyl 4-(3-phenylprop-2-ynyloxy)-3-methoxybenzoate

HRID 1614246Notes

Reaction equation

[C:1]1([C:7]#[C:8][CH2:9]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([O:22][CH2:23][CH3:24])(=[O:21])[C:12]1[CH:20]=[CH:19][C:17]([OH:18])=[C:14]([O:15][CH3:16])[CH:13]=1>>[C:1]1([C:7]#[C:8][CH2:9][O:18][C:17]2[CH:19]=[CH:20][C:12]([C:11]([O:22][CH2:23][CH3:24])=[O:21])=[CH:13][C:14]=2[O:15][CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 12038Ethyl vanillate

HCID 10987157(3-Bromoprop-1-yn-1-yl)benzene

Product 1

HCID 19773090Ethyl 4-(3-phenylprop-2-ynyloxy)-3-methoxybenzoateYield 70%

Procedure

3-Phenylprop-2-ynyl bromide was reacted with ethyl vanillate using the conditions described in Example 1 to give ethyl 4-(3-phenylprop-2-ynyloxy)-3-methoxybenzoate in 70% yield, m.p. 62°-65° C. Following the procedures described in the portion of Example 6 which is concerned with the preparation of starting materials the product so obtained was reacted with thiazol-2-yl-lithium and the resultant product was reacted with ethylmagnesium iodide to give the required starting material as an oil in 61% yield.

Sources & evidence

ORD record: ord-261c6a327ba647e8ac51e559e455d6a5
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196422

Reaction notes

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