(3R,4R)-methyl 4-(3-bromophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

Base Information

Chemical Name:(3R,4R)-methyl 4-(3-bromophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
CAS No.:1267588-59-9
Molecular Formula:C₁₉H₁₅BrO₄
Molecular Weight:387.23
Hs Code.:

Synonyms:(3R,4R)-methyl 4-(3-bromophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

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Chemical Property of (3R,4R)-methyl 4-(3-bromophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

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Technology Process of (3R,4R)-methyl 4-(3-bromophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

There total 3 articles about (3R,4R)-methyl 4-(3-bromophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate 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: 64.0%

: 103-82-2
phenylacetic acid

: 104094-31-7
(E)-methyl 4-(3-bromophenyl)-2-oxobut-3-enoate

: 1267588-59-9
(3R,4R)-methyl 4-(3-bromophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

Guidance literature:: phenylacetic acid; (E)-methyl 4-(3-bromophenyl)-2-oxobut-3-enoate; With pivaloyl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.333333h;

With (2S,3R)-3-isopropyl-2-phenyl-3,4-dihydro-2H-benzo[4,5]thiazolo[3,2-a]pyrimidine; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -30 ℃; for 16h; stereospecific reaction;
DOI:10.1021/ja109975c

Reference yield:

: 3132-99-8
m-bromobenzoic aldehyde

: 1267588-59-9
(3R,4R)-methyl 4-(3-bromophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium hydroxide / methanol / 0 - 40 °C

2.1: acetyl chloride / 0 °C / Reflux

3.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / 0 °C

3.2: 16 h / -30 °C

With pivaloyl chloride; N-ethyl-N,N-diisopropylamine; acetyl chloride; potassium hydroxide; In methanol; dichloromethane;
DOI:10.1021/ja109975c

Reference yield:

: 1267589-63-8
potassium (E)-4-(3-bromophenyl)-2-oxobut-3-enoate

: 1267588-59-9
(3R,4R)-methyl 4-(3-bromophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: acetyl chloride / 0 °C / Reflux

2.1: pivaloyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / 0 °C

2.2: 16 h / -30 °C

With pivaloyl chloride; N-ethyl-N,N-diisopropylamine; acetyl chloride; In dichloromethane;
DOI:10.1021/ja109975c