2,2-Dimethyl-5-(1-methylethylidene)-1,3-dioxane-4,6-dione → 5-(2-(3-Methoxyphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1662556Notes

Reaction equation

HRID 1662556 reaction equation
CC1C=C(COC2C=C(CCC(O)=O)C=CC=2)C=CC=1C1C=CC=C(OC)C=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([Mg]Br)[CH:34]=[CH:35][CH:36]=1.[CH3:39][C:40]1([CH3:51])[O:45][C:44](=[O:46])[C:43](=[C:47]([CH3:49])[CH3:48])[C:42](=[O:50])[O:41]1>>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([C:47]([CH:43]2[C:42](=[O:50])[O:41][C:40]([CH3:39])([CH3:51])[O:45][C:44]2=[O:46])([CH3:49])[CH3:48])[CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 3

HCID 752182,2-Dimethyl-5-(1-methylethylidene)-1,3-dioxane-4,6-dioneHCID 252612983-(3-(((2-Methyl-3'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoic acidHCID 178490745HCID 178490745, compound

Product 1

HCID 577072545-(2-(3-Methoxyphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Procedure

The 5-(2-(3-methoxyphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione (85.C) was prepared via the procedure described in Huang, X.; et. al.; Tetrahedron Letters; 1982, (1); pp. 75-76. from (3-methoxyphenyl)magnesium bromide (1.0 M in THF solution from Aldrich) and 85.B. 1H NMR (400 MHz, CDCl3) ppm 7.26 (1H, t, J=8.0 Hz), 6.94 (1H, d, J=7.8 Hz), 6.89 (1H, t, J=2.2 Hz), 6.79 (1H, dd, J=8.2, 2.3 Hz), 3.81 (3H, s), 3.62 (1H, s), 1.67 (6H, s), 1.66 (3H, s), 1.34 (3H, s).

Sources & evidence

ORD record
ord-d48484c1f17542a7806160f29f287c19
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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