ethyl 3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)-4-trimethylsilylbenzoate

Base Information

Chemical Name:ethyl 3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)-4-trimethylsilylbenzoate
CAS No.:152835-84-2
Molecular Formula:C₂₂H₃₃F₂NO₅Si
Molecular Weight:457.59
Hs Code.:

Synonyms:ethyl 3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)-4-trimethylsilylbenzoate

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Chemical Property of ethyl 3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)-4-trimethylsilylbenzoate

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Technology Process of ethyl 3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)-4-trimethylsilylbenzoate

There total 10 articles about ethyl 3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)-4-trimethylsilylbenzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 367-27-1
2,4-difluorophenol

: 152835-84-2
ethyl 3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)-4-trimethylsilylbenzoate

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / CH₂Cl₂ / 2 h / 10 - 20 °C

2: HNO₃, H₂SO₄ / 1 h / 10 - 20 °C

3: NaHCO₃, methanol / 16 h / Ambient temperature

4: 96 percent / H₂ / 10percent Pd/C / ethyl acetate / 27 h / 50 - 60 °C

5: 91 percent / pyridine / 0.5 h / 0 °C

6: 86 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

7: 1.) LDA / 1.) THF, hexane, from -78 to -55 deg C, 10 min, 2.) THF, hexane, from -78 to -60 deg C, 1 h

8: 1.) BuLi / 1.) THF, hexane, from -55 to -30 deg C, 2.) THF, hexane, -55 deg C, 30 min

With pyridine; methanol; n-butyllithium; sulfuric acid; (1S)-10-camphorsulfonic acid; hydrogen; nitric acid; sodium hydrogencarbonate; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In dichloromethane; ethyl acetate;
DOI:10.1055/s-1997-1379

Reference yield:

: 113512-57-5
2,4-difluoro-5-nitrophenol

: 152835-84-2
ethyl 3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)-4-trimethylsilylbenzoate

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / H₂ / 10percent Pd/C / ethyl acetate / 27 h / 50 - 60 °C

2: 91 percent / pyridine / 0.5 h / 0 °C

3: 86 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

4: 1.) LDA / 1.) THF, hexane, from -78 to -55 deg C, 10 min, 2.) THF, hexane, from -78 to -60 deg C, 1 h

5: 1.) BuLi / 1.) THF, hexane, from -55 to -30 deg C, 2.) THF, hexane, -55 deg C, 30 min

With pyridine; n-butyllithium; (1S)-10-camphorsulfonic acid; hydrogen; lithium diisopropyl amide; palladium on activated charcoal; In dichloromethane; ethyl acetate;
DOI:10.1055/s-1997-1379

Reference yield:

: 152169-43-2
2,4-difluorophenyl ethyl carbonate

: 152835-84-2
ethyl 3,5-difluoro-6-pivaloylamino-2-(2-tetrahydropyranyloxy)-4-trimethylsilylbenzoate

Guidance literature:: Multi-step reaction with 7 steps

1: HNO₃, H₂SO₄ / 1 h / 10 - 20 °C

2: NaHCO₃, methanol / 16 h / Ambient temperature

3: 96 percent / H₂ / 10percent Pd/C / ethyl acetate / 27 h / 50 - 60 °C

4: 91 percent / pyridine / 0.5 h / 0 °C

5: 86 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

6: 1.) LDA / 1.) THF, hexane, from -78 to -55 deg C, 10 min, 2.) THF, hexane, from -78 to -60 deg C, 1 h

7: 1.) BuLi / 1.) THF, hexane, from -55 to -30 deg C, 2.) THF, hexane, -55 deg C, 30 min

With pyridine; methanol; n-butyllithium; sulfuric acid; (1S)-10-camphorsulfonic acid; hydrogen; nitric acid; sodium hydrogencarbonate; lithium diisopropyl amide; palladium on activated charcoal; In dichloromethane; ethyl acetate;
DOI:10.1055/s-1997-1379