Trimethylsilyldiazomethane → Methyl 2-[4-(hydroxymethyl)phenyl]acetate

HRID 1944131Notes

Reaction equation

HRID 1944131 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:14]>CO>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:14])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 32834984-(Hydroxymethyl)phenylacetic acid

Product 1

HCID 12575321Methyl 2-[4-(hydroxymethyl)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2-(4-(hydroxymethyl)phenyl)acetic acid in MeOH at 0° C. was added TMS-CHN2. The solution was stirred for 3 h then quenched with a few drops of AcOH. The solvents were evaporated. Column chromatography (SiO2, 3-15% EtOAc/Hex) gave pure methyl 2-(4-(hydroxymethyl)phenyl)acetate (E132).

Workup

  1. customthen quenched with a few drops of AcOH
  2. customThe solvents were evaporated

Sources & evidence

ORD record
ord-cc34defc08ff4f6e8d58b852fd32190c
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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