Methyl 3-(3-hydroxyphenyl)propionate → Methyl 3-(3-(((2-(1,1-dimethylethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoate

HRID 1662342Notes

Reaction equation

HRID 1662342 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.Cl[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=2[F:30])=[C:18]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:17]=1>>[CH3:34][C:31]([C:18]1[CH:17]=[C:16]([CH2:15][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=2)[CH:21]=[CH:20][C:19]=1[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[F:30])([CH3:32])[CH3:33]

Participants

3

Reactant 2

HCID 1512675Methyl 3-(3-hydroxyphenyl)propionateHCID 577056714-(Chloromethyl)-2-(1,1-dimethylethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl

Product 1

HCID 57706370Methyl 3-(3-(((2-(1,1-dimethylethyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoateYield 83%

Procedure

Methyl 3-(3-hydroxyphenyl)propanoate (commercially available from Aagile Labs Division of Tyger Scientific) (0.025 g, 0.14 mmol) was alkylated by reaction with compound 8.10 (0.043 g, 0.14 mmol) according to the method given in Example 1 to give compound 34.1 as a clear oil (0.052 g, 83% yield). MS ESI (pos.) m/e: 473.2 (M+Na)+, 468.2 (M+H2O)+.

Sources & evidence

ORD record
ord-81fe2f87f75e4b97ad8da0aec0ee8f0d
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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