(2S)-2-(2,4-difluorophenyl)-2-[(tetrahydropyran-2-yloxy)methyl]oxirane

Base Information

Chemical Name:(2S)-2-(2,4-difluorophenyl)-2-[(tetrahydropyran-2-yloxy)methyl]oxirane
CAS No.:310882-23-6
Molecular Formula:C₁₄H₁₆F₂O₃
Molecular Weight:270.276
Hs Code.:

Synonyms:

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Chemical Property of (2S)-2-(2,4-difluorophenyl)-2-[(tetrahydropyran-2-yloxy)methyl]oxirane

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Technology Process of (2S)-2-(2,4-difluorophenyl)-2-[(tetrahydropyran-2-yloxy)methyl]oxirane

There total 1 articles about (2S)-2-(2,4-difluorophenyl)-2-[(tetrahydropyran-2-yloxy)methyl]oxirane 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:

: 110-87-2
3,4-dihydro-2H-pyran

: 141113-37-3
(S)-(2-(2,4-difluorophenyl)oxiran-2-yl)methanol

: 310882-23-6
(2S)-2-(2,4-difluorophenyl)-2-[(tetrahydropyran-2-yloxy)methyl]oxirane

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

: 310882-23-6
(2S)-2-(2,4-difluorophenyl)-2-[(tetrahydropyran-2-yloxy)methyl]oxirane

: 310882-17-8
(2R-cis)-2-(2,4-difluorophenyl)-2-hydroxymethyl-4-(5-methyl-4-oxohexyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran / 24 h / 50 - 60 °C

1.2: 6.36 g / p-toluenesulfonic acid monohydrate / methanol / 0.5 h / 20 °C

2.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

3.1: 5.15 g / NaH / dimethylformamide / 4 h / 20 °C

4.1: NaH; DMSO / 1 h / 20 °C

4.2: 85.9 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

5.1: 94.8 percent / NaBH₄; LiCl / ethanol / 28 h / 20 °C

6.1: 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 15.5 h / 20 °C

7.1: 1.50 g / NaH / toluene / 4 h / Heating

8.1: 88.8 percent / dimethylsulfoxide / 15 h / 55 °C

9.1: 64.1 percent / diisobutylaluminum hydride / toluene / -78 - 20 °C

10.1: 1,8-diazabicyclo[5,4,0]undecen-7-ene; LiCl / acetonitrile / 3 h / 20 °C

11.1: 362 mg / H₂ / Pd/C / ethanol / 20 °C

With dmap; sodium tetrahydroborate; 1,8-diazabicyclo[5.4.0]-undecen-7-ene; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Ring cleavage / 1.2: methanolysis / 2.1: mesylation / 3.1: Cyclization / 4.1: Metallation / 4.2: Ring cleavage / 5.1: Reduction / 6.1: Tosylation / 7.1: Cyclization / 8.1: Substitution / 9.1: Reduction / 10.1: Horner-Wadsworth-Emmons reaction / 11.1: Catalytic hydrogenation;
DOI:10.1016/S0968-0896(00)00177-2

Reference yield:

: 310882-23-6
(2S)-2-(2,4-difluorophenyl)-2-[(tetrahydropyran-2-yloxy)methyl]oxirane

: 310882-35-0
(2R-trans)-2-(2,4-difluorophenyl)-2-hydroxymethyl-4-(5-methyl-4-oxohexyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran / 24 h / 50 - 60 °C

1.2: 6.36 g / p-toluenesulfonic acid monohydrate / methanol / 0.5 h / 20 °C

2.1: Et₃N / CH₂Cl₂ / 2 h / 20 °C

3.1: 5.15 g / NaH / dimethylformamide / 4 h / 20 °C

4.1: NaH; DMSO / 1 h / 20 °C

4.2: 85.9 percent / dimethylsulfoxide / 30 h / 75 - 80 °C

5.1: 94.8 percent / NaBH₄; LiCl / ethanol / 28 h / 20 °C

6.1: 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 15.5 h / 20 °C

7.1: 2.19 g / NaH / toluene / 4 h / Heating

8.1: 95.1 percent / dimethylsulfoxide / 15 h / 55 °C

9.1: 74.2 percent / diisobutylaluminum hydride / toluene / -78 - 20 °C

10.1: 1,8-diazabicyclo[5,4,0]undecen-7-ene; LiCl / acetonitrile / 3 h / 20 °C

11.1: 568 mg / H₂ / Pd/C / ethanol / 20 °C

With dmap; sodium tetrahydroborate; 1,8-diazabicyclo[5.4.0]-undecen-7-ene; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Ring cleavage / 1.2: methanolysis / 2.1: mesylation / 3.1: Cyclization / 4.1: Metallation / 4.2: Ring cleavage / 5.1: Reduction / 6.1: Tosylation / 7.1: Cyclization / 8.1: Substitution / 9.1: Reduction / 10.1: Horner-Wadsworth-Emmons reaction / 11.1: Catalytic hydrogenation;
DOI:10.1016/S0968-0896(00)00177-2