ChemicalBook CAS DataBase List methyl 6-(trifluoromethylsulfonyloxy)-1-naphthoate

methyl 6-(trifluoromethylsulfonyloxy)-1-naphthoate synthesis

5synthesis methods

Product Name:methyl 6-(trifluoromethylsulfonyloxy)-1-naphthoate
CAS Number:255050-65-8
Molecular formula:C13H9F3O5S
Molecular Weight:334.27

The synthesis of methyl 6-(trifluoromethylsulfonyloxy)-1-naphthoate is as follows:
Diisopropylethyiamine (2.35 mL, 13,5 mmol) and irifluoromethanesuifonic anhydride (0,95 mL, 5.6 mmol) were added sequentially to a solution of methyl 6-hydroxy- l- naphthoate ( 10 mg, 4.5 mmol) in CH2C12 (60 mL) at - 78 °C. After 1 h at - 78 °C, the reaction mixture was poured into saturated aqueous NH4C1 (30 mL). The resulting mixture was extracted with CH2CI2 (3x50 mL). The combined organic phase was washed with brine (50 mL) then dried ( a2S0 ), filtered and concentrated in vacuo. The resulting residue was purified on 80 g silica gel (100% hexanes - 100% EtOAc, gradient) to afford 1 ,45 g (96%) of methyl 6-(trifluoromethylsulfonyloxy)-1-naphthoate.
synthesis of methyl 6-(trifluoromethylsulfonyloxy)-1-naphthoate.png

synthesis of methyl 6-(trifluoromethylsulfonyloxy)-1-naphthoate.png

358-23-6 Synthesis

358-23-6
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90162-13-3 Synthesis

6-Hydroxy-naphthalene-1-carboxylic acid Methyl ester

90162-13-3
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methyl 6-(trifluoromethylsulfonyloxy)-1-naphthoate

255050-65-8
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Yield:255050-65-8 96%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in dichloromethane at -78; for 1 h;

Steps:

1; 1.2

Diisopropylethyiamine (2.35 mL, 13,5 mmol) and irifluoromethanesuifonic anhydride (0,95 mL, 5.6 mmol) were added sequentially to a solution of methyl 6-hydroxy- l- naphthoate ( 10 mg, 4.5 mmol) in CH₂C1₂ (60 mL) at - 78 °C. After 1 h at - 78 °C, the reaction mixture was poured into saturated aqueous NH₄C1 (30 mL). The resulting mixture was extracted with CH₂CI₂ (3x50 mL). The combined organic phase was washed with brine (50 mL) then dried ( a₂S0 ), filtered and concentrated in vacuo. The resulting residue was purified on 80 g silica gel (100% hexanes - 100% EtOAc, gradient) to afford 1 ,45 g (96%) of methyl 6-(((irifluoromethyl)s?lfony.)oxy)-l -naphthoate.

References:

WO2012/3145,2012,A2 Location in patent:Page/Page column 9; 20

37595-74-7 Synthesis