3-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehyde → (3-((3-((1,3-Dioxolan-2-yl)methyl)benzyl)oxy)phenyl)(3-fluorophenyl)methanol

HRID 332669Notes

Reaction equation

HRID 332669 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[O:10]1[CH2:14][CH2:13][O:12][CH:11]1[CH2:15][C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25].O1CCOC1CCCCCCCCOC1C=C(C=CC=1)C=O>>[O:10]1[CH2:14][CH2:13][O:12][CH:11]1[CH2:15][C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH:24]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[OH:25])[CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 866768973-(8-(1,3-Dioxolan-2-yl)octyloxy)benzaldehydeHCID 866769033-((3-((1,3-Dioxolan-2-yl)methyl)benzyl)oxy)benzaldehydeHCID 178505773HCID 178505773, compound

Product 1

HCID 71113239(3-((3-((1,3-Dioxolan-2-yl)methyl)benzyl)oxy)phenyl)(3-fluorophenyl)methanol

Procedure

The title compound was prepared as described in Example 10 Step 2 with 3-fluorophenylmagnesium bromide and 3-((3-((1,3-dioxolan-2-yl)methyl)benzyl)oxy)-benzaldehyde replacing 2-thienylmagnesium bromide and 3-(8-(1,3-dioxolan-2-yl)octyloxy)benzaldehyde, respectively.

Sources & evidence

ORD record
ord-46ab887496e848edb23fdf7f6169d872
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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