5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester

Base Information

Chemical Name:5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester
CAS No.:913626-20-7
Molecular Formula:C₁₉H₂₅BrO₄
Molecular Weight:397.309
Hs Code.:

5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid <i>tert</i>-butyl ester

Synonyms:5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester

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Chemical Property of 5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester

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Technology Process of 5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester

There total 2 articles about 5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester 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: 96.0%

: 913626-19-4
3-[(1S)-1-(4-bromo-phenyl)-but-3-enyloxy]-propionitrile

: 5292-43-3
bromoacetic acid tert-butyl ester

: 913626-20-7
5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester

Guidance literature:: With zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; at 60 ℃; for 4h;
DOI:10.1021/ol0618149

Reference yield:

: 221898-37-9
(S)-1-(4-bromophenyl)but-3-en-1-ol

: 913626-20-7
5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 599 mg / Triton B / CH₂Cl₂; H₂O / 2 h / 20 - 25 °C

2: 96 percent / zinc / Cp₂TiCl₂ / tetrahydrofuran / 4 h / 60 °C

With N-benzyl-trimethylammonium hydroxide; zinc; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; dichloromethane; water; 2: Blaise reaction;
DOI:10.1021/ol0618149

Reference yield:

: 913626-20-7
5-[1-(4-bromo-phenyl)-but-3-enyloxy]-3-oxo-pentanoic acid tert-butyl ester

: Octanoic acid (E)-(1S,5S,9S,11S,15R,19R,21S,24S)-1,15-dihydroxy-19-hydroxymethyl-23-[1-methoxycarbonyl-meth-(E)-ylidene]-2,2-dimethyl-17-oxo-11-phenyl-6,12,18,25,26-pentaoxa-tricyclo[19.3.1.1^5,9]hexacos-3-en-24-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: ozone / CH₂Cl₂ / 0.08 h / -78 °C

1.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

2.1: 1.8219 g / SnCl₄ / CH₂Cl₂ / 3.33 h / -78 - 25 °C

3.1: NaBH₄ / methanol / 0.33 h / 0 °C

4.1: 70 percent / lithium triethylborohydride / tetrahydrofuran / 1.75 h / 0 - 25 °C

5.1: 81 percent / 2,6-lutidine / CH₂Cl₂ / 23.67 h / -30 - 25 °C

6.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / toluene / 4 h / 20 - 25 °C

6.2: 81 percent / DMAP / toluene / 1.75 h / 20 - 25 °C

7.1: 83 percent / HF*pyridine / tetrahydrofuran / 5.5 h / 0 - 25 °C

8.1: 24 percent / CsF / Pd(OAc)2; 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)-biphenyl / dioxane / 53.8 h / 20 - 25 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; 2,4,6-trichlorobenzoyl chloride; tin(IV) chloride; lithium triethylborohydride; pyridine hydrogenfluoride; ozone; triethylamine; cesium fluoride; palladium diacetate; DavePhos; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; 2.1: Roskamp homologation / 8.1: Suzuki coupling;
DOI:10.1021/ol0618149