Dichloromethane → HCID 57936580, compound

HRID 1434877Notes

Reaction equation

HRID 1434877 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][S:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:14](Cl)Cl.C[Si](C=[N+]=[N-])(C)C.CCCCCC>CO>[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][S:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 57936575HCID 57936575, compound

Product 1

HCID 57936580HCID 57936580, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-hydroxy-4-(methylthiomethyl)benzoic acid (3.96 g, 20 mmol), CH2Cl2 (75 mL), and MeOH (15 mL) was added a solution of 2 M trimethylsilyldiazomethane (TMSCHN2) in hexane (10.5 mL, 21 mmol) over 30 min. After stirring for 10 min, the reaction was concentrated and vacuum dried. The residue was chromatographed (250 g SiO2, hexanes to 5% EtOAc/hexanes) to give the title compound as a colorless oil (3.96 g, 93%).

Workup

  1. concentrationthe reaction was concentrated
  2. customvacuum dried
  3. customThe residue was chromatographed (250 g SiO2, hexanes to 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-32e23533a9624231a77187d0de2ec82a
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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