5-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 5-(1-(3-Hydroxyphenyl)-2-methyl-2-propenyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1662359Notes

Reaction equation

HRID 1662359 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]2[C:14](=[O:15])[O:13][C:12]([CH3:17])([CH3:16])[O:11][C:10]2=[O:18])[CH:5]=[CH:6][CH:7]=1.[C:19]([Mg]Br)([CH3:21])=[CH2:20].OC1C=C(C(C2C(=O)OC(C)(C)OC2=O)CC=C)C=CC=1>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH:9]2[C:10](=[O:18])[O:11][C:12]([CH3:16])([CH3:17])[O:13][C:14]2=[O:15])[C:19]([CH3:21])=[CH2:20])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6053805-(3-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 577059815-(1-(3-Hydroxyphenyl)-3-butenyl)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 178456138HCID 178456138, compound

Product 1

HCID 577057455-(1-(3-Hydroxyphenyl)-2-methyl-2-propenyl)-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 38%

Procedure

Compound 8.1 (2.00 g, 8.1 mmol) was treated with isopropenylmagnesium bromide (available from Aldrich) (0.5 M in THF) (97 mL, 48 mmol) according to the method described for preparation of 43.1 to afford 48.1 (0.88 g, 38%) as a yellow oil.

Sources & evidence

ORD record
ord-617a99b248094b4c83e04c9296abfcc2
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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