Diisobutylaluminum hydride → (E)-3-(2-methoxyphenyl)prop-2-en-1-ol

HRID 14431ノート

反応式

HRID 14431 の反応式
CC(C[AlH]CC(C)C)C.COC1C=CC(/C=C/C=O)=CC=1.[CH3:22][O:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1/[CH:26]=[CH:27]/[CH:28]=[O:29]>N1C=CC=CC=1>[CH3:22][O:23][C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1/[CH:26]=[CH:27]/[CH2:28][OH:29]

参加物

5

反応物 3

HCID 14487Diisobutylaluminum hydrideHCID 641294p-METHOXYCINNAMALDEHYDEHCID 641298O-Methoxycinnamaldehyde, (E)-

生成物 1

HCID 11400969(E)-3-(2-methoxyphenyl)prop-2-en-1-ol

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

[Ir(cod)Cl]2, O,O′-(R)-(1,1′-Dinaphthyl-2,2′-diyl)-N,N′-di-(R,R)-phenylethylphosphoramidite were prepared according to published procedures (Herde, J. L.; Lambert, J. C.; Senoff, C. V. Inorg. Synth. 1974, 15, 18; Alexakis, A.; Rosset, S.; Allamand, J.; March, S.; Guillen, F.; Benhaim, C. Synlett 2001, 1375). Lithium aryloxides were prepared by reaction of the corresponding phenols with n-BuLi in THF at 0° C. After being stirred for 10 min at room temperature, the solution was concentrated under vacuum to afford the corresponding lithium aryloxides as white powders, which were stored under inert atmosphere. All allylic carbonates were synthesized by the reaction of the corresponding allylic alcohols with the corresponding alkylchloroformate in the presence of pyridine. (E)-4-Methoxycinnamamyl alcohol and (E)-2-methoxycinnamyl alcohol were prepared by the reduction of the corresponding aldehydes with DIBAL-H (Nung Min, Y.; Young Soo, G. J. Org. Chem. 1985, 50, 2443). Phenols, (E)-4-methoxycinnamaldehyde, and (E)-2-methoxycinnamaldehyde were purchased from Aldrich Chemicals Co. and used without further purification.

後処理

  1. customand used without further purification

出典と根拠

ORDレコード
ord-4b393935e3d94bf5b71cc2c2bafb20aa
出典データセット
uspto-grants-2010_06
特許番号
US07732365B2

反応ノート

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