4-Bromo-benzoic acid (3R,3aS,6aR)-3a-ethyl-6a-hydroxymethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

Base Information

Chemical Name:4-Bromo-benzoic acid (3R,3aS,6aR)-3a-ethyl-6a-hydroxymethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester
CAS No.:477772-17-1
Molecular Formula:C₁₆H₁₇BrO₆
Molecular Weight:385.211
Hs Code.:

Synonyms:4-Bromo-benzoic acid (3R,3aS,6aR)-3a-ethyl-6a-hydroxymethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

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Chemical Property of 4-Bromo-benzoic acid (3R,3aS,6aR)-3a-ethyl-6a-hydroxymethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

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Technology Process of 4-Bromo-benzoic acid (3R,3aS,6aR)-3a-ethyl-6a-hydroxymethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

There total 8 articles about 4-Bromo-benzoic acid (3R,3aS,6aR)-3a-ethyl-6a-hydroxymethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl 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: 98.0%

: 477772-16-0
4-bromo-benzoic acid 6a-(tert-butyl-dimethyl-silanyloxymethyl)-3a-ethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

: 477772-17-1
4-Bromo-benzoic acid (3R,3aS,6aR)-3a-ethyl-6a-hydroxymethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1039/b205924j

Reference yield:

: 586-75-4
4-chlorobenzoyl chloride

: 477772-17-1
4-Bromo-benzoic acid (3R,3aS,6aR)-3a-ethyl-6a-hydroxymethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 98 percent / aq. HCl / tetrahydrofuran / 24 h / 20 °C

With pyridine; hydrogenchloride; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b205924j

Reference yield:

: 403665-44-1
(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-furan-3-yl-propan-1-ol

: 477772-17-1
4-Bromo-benzoic acid (3R,3aS,6aR)-3a-ethyl-6a-hydroxymethyl-5-oxo-hexahydro-furo[3,2-b]furan-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 96 percent / imidazole; DMAP / dimethylformamide / 0.5 h / 20 °C

2.1: n-BuLi / tetrahydrofuran / -78 °C

2.2: 80 percent / tetrahydrofuran / 0.08 h / -78 °C

3.1: 76 percent / aq. peracetic acid; NaOAc / CH₂Cl₂ / 48 h / 0 - 20 °C

4.1: 93 percent / aq. acetic acid / 24 h / 20 °C

5.1: Et₃N / toluene / 72 h / Heating

5.2: aq. HCl / 48 h / 20 °C

5.3: 45 percent / imidazole; DMAP / dimethylformamide / 1 h / 0 °C

6.1: 90 percent / pyridine / CH₂Cl₂ / 24 h / 20 °C

7.1: 98 percent / aq. HCl / tetrahydrofuran / 24 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; peracetic acid; dmap; n-butyllithium; sodium acetate; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Michael addition;
DOI:10.1039/b205924j