Allyl bromide → HCID 19773037, compound

HRID 1614239Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([OH:13])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=1.[CH2:26](Br)[CH:27]=[CH2:28]>>[CH2:28]([O:1][C:2]1[CH:12]=[C:11]([O:13][CH2:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[CH:10]=[C:4]([CH:3]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:27]=[CH2:26]

Participants

Reactant 3

HCID 7841Allyl bromide

HCID 20098Benzoic acid, 3,5-dihydroxy-, ethyl ester

HCID 703202-Bromomethylnaphthalene

Product 1

HCID 19773037HCID 19773037, compoundYield 15%

Procedure

Ethyl 3,5-dihydroxybenzoate was reacted in turn with 2-bromomethylnaphthalene and allyl bromide using the conditions described in Example 1 to give ethyl 5-allyloxy-3-(naphth-2-ylmethoxy)benzoate in 15% yield, as an oil. Following the procedures described in the portion of Example 3 which is concerned with the preparation of starting materials the product so obtained was reacted with thiazol-2-yl-lithium to give 5-allyloxy-3-(naphth-2-ylmethoxy)phenyl 2-thiazolyl ketone in 52% yield, m.p. 65°-67° C., and that product was reacted with ethylmagnesium to give the required starting material in 49% yield, as a gum.

Sources & evidence

ORD record: ord-978a2252105a4688baa9f58642802d57
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196422

Reaction notes

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