(4S,5S)-5-[(E)-3-chloroprop-1-enyl]-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazole

Base Information

Chemical Name:(4S,5S)-5-[(E)-3-chloroprop-1-enyl]-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazole
CAS No.:938449-00-4
Molecular Formula:C₁₉H₂₄ClNO
Molecular Weight:317.859
Hs Code.:

Synonyms:(4S,5S)-5-[(E)-3-chloroprop-1-enyl]-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazole

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Chemical Property of (4S,5S)-5-[(E)-3-chloroprop-1-enyl]-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazole

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Technology Process of (4S,5S)-5-[(E)-3-chloroprop-1-enyl]-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazole

There total 3 articles about (4S,5S)-5-[(E)-3-chloroprop-1-enyl]-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazole 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: 91.0%

: 938448-96-5
(E)-3-[(4S,5S)-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazol-5-yl]prop-2-en-1-ol

: 938449-00-4
(4S,5S)-5-[(E)-3-chloroprop-1-enyl]-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazole

Guidance literature:: With dmap; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1002/ejoc.200600927

Reference yield:

: 938448-92-1
methyl (E)-3-[(4S,5S)-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazol-5-yl]acrylate

: 938449-00-4
(4S,5S)-5-[(E)-3-chloroprop-1-enyl]-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazole

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / i-Bu₂AlH / tetrahydrofuran; hexane / 2 h / -78 °C

2: 91 percent / p-toluenesulfonyl chloride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

With dmap; diisobutylaluminium hydride; p-toluenesulfonyl chloride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/ejoc.200600927

Reference yield:

: 257296-67-6
(4S-trans)-4,5-dihydro-4-cyclohexylmethyl-2-phenyl-5-vinyloxazoline

: 938449-00-4
(4S,5S)-5-[(E)-3-chloroprop-1-enyl]-4-(cyclohexylmethyl)-4,5-dihydro-2-phenyloxazole

Guidance literature:: Multi-step reaction with 3 steps

1.1: ozone / methanol / -78 °C

1.2: 84 percent / LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h

2.1: 99 percent / i-Bu₂AlH / tetrahydrofuran; hexane / 2 h / -78 °C

3.1: 91 percent / p-toluenesulfonyl chloride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

With dmap; diisobutylaluminium hydride; ozone; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1002/ejoc.200600927