Trimethylsilyldiazomethane → Methyl 2-(hydroxymethyl)-2'-methylbiphenyl-4-carboxylate

HRID 2410485Notes

Reaction equation

HRID 2410485 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[OH:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25]>CO.C1(C)C=CC=CC=1>[OH:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:1])=[O:17])[CH:13]=[CH:12][C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 594957342-(Hydroxymethyl)-2'-methylbiphenyl-4-carboxylic acid

Product 1

HCID 66678471Methyl 2-(hydroxymethyl)-2'-methylbiphenyl-4-carboxylateYield 98.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

(Trimethylsilyl)diazomethane (21 mL, 12.4 mmol) was added dropwise into a solution of 2-(hydroxymethyl)-2′-methylbiphenyl-4-carboxylic acid (2.0 g, 8.3 mmol) in MeOH (20 mL) and toluene (20 mL) at 0° C. After 10 minutes at 0° C., the resulting mixture was stirred at RT for 2 hours. The reaction mixture was concentrated under vacuum to give the title compound (2.1 g, quantitative), used without further purification in the next step. HPLC (Method A) Rt 3.95 min (purity 95.5%). 1H NMR (CDCl3, 300 MHz) δ 8.23 (d, J=1.3 Hz, 1H), 7.98 (dd, J=7.8, 1.9 Hz, 1H), 7.28-7.18 (m, 4H), 7.08 (d, J=7.3 Hz, 1H), 4.42 (d, J=5.7 Hz, 2H), 3.92 (s, 3H), 2.01 (s, 3H), 1.61 (t, J=5.7 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-36a08c4f6a184c7fa71e13d9b75b65f9
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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