Methanesulfonic Acid → HCID 57276568、化合物

反応式

CS(O)(=O)=O.[C:6]1([C:12]#[CH:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:14][O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH2:17].C[O:25][C:26](OC)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:27]>>[CH3:14][O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:17][C:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:13].[C:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:25])[CH3:27].[C:6]1([C:12]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

反応物 4

HCID 6395Methanesulfonic Acid

HCID 10821Phenylacetylene

HCID 78008Benzene, (1,1-dimethoxyethyl)-

HCID 521220Benzene, (1-methoxyethenyl)-2 回

生成物 3

HCID 7410Acetophenone収率 4%

HCID 119301,3,5-Triphenylbenzene収率 2%

HCID 57276568HCID 57276568、化合物収率 13%

反応条件

温度: 40 °C

実験手順

In a flask equipped with thermometer and reflux condenser, methanol (8.01 g, 250 mmol) and phenylacetylene (6.38 g, 62.5 mmol) were provided and heated to 40° C. Triphenylphosphine gold(I) methyl (14.8 mg, 31.2 μmol) and methanesulfonic acid (40.6 μl, 625 μmol) were then added in rapid succession. After a reaction time of 8 h, 99% of the phenylacetylene had been converted. The main products formed were α-methoxystyrene (selectivity (S)=61%) and acetophenone dimethyl ketal (S=20%). Subsequent acid-catalyzed reaction of the α-methoxystyrene by-produced 1-methoxy-1,3-diphenylbutadiene (as 1:1 cis/trans mixture, S=13%) acetophenone (S=4%) and 1,3,5-triphenylbenzene (S=2%).

後処理

customThe main products formed

出典と根拠

ORDレコード: ord-548342e771934e52a863124fb6fd9dbf
出典データセット: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06037482

反応ノート

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