Methanol → HCID 81654350, compound

HRID 1028487Notes

Reaction equation

HRID 1028487 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:13]([OH:17])[C:14]([OH:16])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CO.[CH3:22][Si](C=[N+]=[N-])(C)C>C1C=CC=CC=1>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[C:5]([CH:13]([OH:17])[C:14]([O:16][CH3:22])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 27567432-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxyacetic acid

Product 1

HCID 81654350HCID 81654350, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To solution of [3,5-bis(trifluoromethyl)phenyl](hydroxy)acetic acid (510 mg, 1.77 mmol) in benzene (10 mL) was added MeOH (1.5 mL) followed by (trimethylsilyl)diazomethane (1.06 mL of a 2M solution in hexanes, 2.12 mmol). After 10 minutes, the reaction was quenched with several drops of HOAc (add until yellow color disappears). The reaction was concentrated and purified by flash chromatography with 10 to 80% EtOAc/hexanes to afford methyl [3,5-bis(trifluoromethyl)phenyl](hydroxy)acetate. 1H NMR (CDCl3, 500 MHz) δ 7.94 (s, 2H), 7.85 (s, 1H), 5.32 (s, 1H), 3.83 (s, 3H), 3.68 (bs, 1H).

Workup

  1. customthe reaction was quenched with several drops of HOAc (add until yellow color disappears)
  2. concentrationThe reaction was concentrated
  3. custompurified by flash chromatography with 10 to 80% EtOAc/hexanes

Sources & evidence

ORD record
ord-94bbe22936ad4fe3b83d1366f3545b94
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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