2-((E)-2-Bromo-3-phenyl-allyl)-2-((1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxa-tricyclo[6.2.1.0^1,6]undec-4-ylmethyl)-malonic acid diethyl ester

Base Information

• Chemical Name: 2-((E)-2-Bromo-3-phenyl-allyl)-2-((1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxa-tricyclo[6.2.1.0^1,6]undec-4-ylmethyl)-malonic acid diethyl ester
• CAS No.: 186038-34-6
• Molecular Formula: C₃₀H₄₁BrO₆
• Molecular Weight: 577.556

Synonyms:2-((E)-2-Bromo-3-phenyl-allyl)-2-((1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxa-tricyclo[6.2.1.0^1,6]undec-4-ylmethyl)-malonic acid diethyl ester

Chemical Property of 2-((E)-2-Bromo-3-phenyl-allyl)-2-((1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxa-tricyclo[6.2.1.0^1,6]undec-4-ylmethyl)-malonic acid diethyl ester

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Technology Process of 2-((E)-2-Bromo-3-phenyl-allyl)-2-((1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxa-tricyclo[6.2.1.0^1,6]undec-4-ylmethyl)-malonic acid diethyl ester

There total 7 articles about 2-((E)-2-Bromo-3-phenyl-allyl)-2-((1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxa-tricyclo[6.2.1.0^1,6]undec-4-ylmethyl)-malonic acid diethyl 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: 49.0%

(1R,2S,4S)-7,7-Dimethyl-1-(1-methyl-1-trimethylsilanyloxy-ethyl)-2-trimethylsilanyloxy-bicyclo[2.2.1]heptane + 2-((Z)-2-Bromo-3-phenyl-allyl)-2-(2-oxo-ethyl)-malonic acid diethyl ester → 2-((E)-2-Bromo-3-phenyl-allyl)-2-((1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxa-tricyclo[6.2.1.01,6]undec-4-ylmethyl)-malonic acid diethyl ester (186038-34-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 10h;

DOI:10.1021/jo961750n

Reference yield:

(-)-(1R)-7,7-dimethyl-2-oxo-1-norbornanecarboxylic acid (64234-14-6) → 2-((E)-2-Bromo-3-phenyl-allyl)-2-((1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxa-tricyclo[6.2.1.01,6]undec-4-ylmethyl)-malonic acid diethyl ester (186038-34-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) (COCl)2, 2.) pyridine / 1.) DMF

2: 74 percent / L-selectride

3: 84 percent / lutidine / 0 °C

4: 41 percent / 0 °C

5: 95 percent / TBAF / tetrahydrofuran / Ambient temperature

6: 89 percent / HMDS, pyridine

7: 49 percent / TMS triflate / CH₂Cl₂ / 10 h / 0 - 20 °C

With pyridine; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; lutidine; tetrabutyl ammonium fluoride; L-Selectride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo961750n

Reference yield:

(1R,2S,4S)-1-(1-Hydroxy-1-methyl-ethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-ol → 2-((E)-2-Bromo-3-phenyl-allyl)-2-((1R,4S,6S,8S)-2,2,11,11-tetramethyl-3,5-dioxa-tricyclo[6.2.1.01,6]undec-4-ylmethyl)-malonic acid diethyl ester (186038-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / HMDS, pyridine

2: 49 percent / TMS triflate / CH₂Cl₂ / 10 h / 0 - 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;

DOI:10.1021/jo961750n

upstream raw materials:

(-)-(1R)-7,7-dimethyl-2-oxo-1-norbornanecarboxylic acid

(1R,4S)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carboxylic acid methyl ester

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