6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole

Base Information

• Chemical Name: 6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole
• CAS No.: 1402436-25-2
• Molecular Formula: C₁₈H₂₁BrO₅
• Molecular Weight: 397.266

Synonyms:6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property of 6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

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Technology Process of 6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole

There total 5 articles about 6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole 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: 80.0%

(3aR,5R,6S,6aR)-[6-(2-bromobenzyloxy)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]methanol (1030614-06-2) + propargyl bromide (106-96-7) → 6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole (1402436-25-2)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water; at 0 - 20 ℃;

DOI:10.1002/adsc.201100988

Reference yield:

1-Bromo-2-bromomethyl-benzene (3433-80-5) → 6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole (1402436-25-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane / 0 - 20 °C

1.2: 20 °C

2.1: water; acetic acid / 8 h / 20 °C

3.1: silica-supported NaIO₄ / dichloromethane / 0.5 h / 20 °C

4.1: sodium tetrahydroborate / methanol / 20 °C

5.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0 - 20 °C

With sodium tetrahydroborate; tetrabutylammomium bromide; water; acetic acid; sodium hydroxide; In methanol; dichloromethane; water;

DOI:10.1002/adsc.201100988

Reference yield:

1-(6-(2-bromobenzyloxy)tetrahydro-2,2-dimethylfuro[3,2-d][1,3]dioxol-5-yl)ethane-1,2-diol (200346-54-9) → 6-(2-bromobenzyloxy)-2,2-dimethyl-5-prop-2-ynyloxymethyltetrahydrofuro[2,3-d][1,3]dioxole (1402436-25-2)

Guidance literature:

Multi-step reaction with 3 steps

1: silica-supported NaIO₄ / dichloromethane / 0.5 h / 20 °C

2: sodium tetrahydroborate / methanol / 20 °C

3: tetrabutylammomium bromide; sodium hydroxide / dichloromethane; water / 0 - 20 °C

With sodium tetrahydroborate; tetrabutylammomium bromide; sodium hydroxide; In methanol; dichloromethane; water;

DOI:10.1002/adsc.201100988

upstream raw materials:

(3aR,5R,6S,6aR)-[6-(2-bromobenzyloxy)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]methanol

propargyl bromide

1-(6-(2-bromobenzyloxy)tetrahydro-2,2-dimethylfuro[3,2-d][1,3]dioxol-5-yl)ethane-1,2-diol

(3aR,5R,6S,6aR)-6-(2-bromo-benzyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

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