(+)-pinanediol (1S)-1-chloro-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate

Base Information

• Chemical Name: (+)-pinanediol (1S)-1-chloro-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate
• CAS No.: 497258-61-4
• Molecular Formula: C₂₂H₂₉BClNO₃
• Molecular Weight: 401.741
• Mol file: 497258-61-4.mol

Synonyms:(+)-pinanediol (1S)-1-chloro-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate

Chemical Property of (+)-pinanediol (1S)-1-chloro-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-pinanediol (1S)-1-chloro-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate

There total 4 articles about (+)-pinanediol (1S)-1-chloro-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate 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:

dichloromethane (75-09-2) + (+)-pinanediol 3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenylboronate (497258-60-3) → (+)-pinanediol (1S)-1-chloro-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate (497258-61-4)

Guidance literature:

dichloromethane; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.5h;

(+)-pinanediol 3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenylboronate; In tetrahydrofuran; hexane; at -100 - 20 ℃; Further stages.;

DOI:10.1021/ja0288338

Reference yield:

(dichloromethyl)lithium (2146-67-0) + (+)-pinanediol 3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenylboronate (497258-60-3) → (+)-pinanediol (1S)-1-chloro-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate (497258-61-4)

Guidance literature:

In tetrahydrofuran; hexane; at -100 - 20 ℃;

Reference yield:

2-(3-bromophenyl)-4,4-dimethyl-2-oxazoline (51849-84-4) → (+)-pinanediol (1S)-1-chloro-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate (497258-61-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: hexane; tetrahydrofuran / 1.5 h / -78 °C

2.1: 1.14 g / hexane; tetrahydrofuran; diethyl ether / 20 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -100 °C

3.2: hexane; tetrahydrofuran / -100 - 20 °C

With n-butyllithium; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/ja0288338

upstream raw materials:

dichloromethane

(+)-pinanediol 3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenylboronate

2-(3-bromophenyl)-4,4-dimethyl-2-oxazoline

(dichloromethyl)lithium

Downstream raw materials:

(+)-pinanediol (1R)-1-(N-bis-trimethylsilylamino)-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate

(+)-pinanediol (1R)-1-acetylamino-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate

(+)-pinanediol (1R)-1-(2-thienylacetylamino)-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate

(+)-pinanediol (1R)-1-{[3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl]amino}-1-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)phenyl]methylboronate