9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one → 4-(2,4-Dichloro-benzylidene)-9,10-dihydro-4h-1-thia-benzo[f]azulene

HRID 2218724

反応式

HRID 2218724 の反応式
[S:1]1[C:10]2[CH2:9][CH2:8][C:7]3[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=3[C:5](=O)[C:4]=2[CH:3]=[CH:2]1.[Cl:16][C:17]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:18]=1[CH2:19][Mg]Cl>C1COCC1>[Cl:16][C:17]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:18]=1[CH:19]=[C:5]1[C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[CH2:8][CH2:9][C:10]2[S:1][CH:2]=[CH:3][C:4]1=2

参加物

4

反応物 2

HCID 7684929,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-oneHCID 178478998HCID 178478998、化合物

生成物 1

HCID 689373754-(2,4-Dichloro-benzylidene)-9,10-dihydro-4h-1-thia-benzo[f]azulene収率 44.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Following the procedures essentially as described in Example 238 and using 9,10-dihydro-1-thia-benzo[f]azulene-4-one (40.8 mg, 0.19 mmol) and 2,4-dichlorobenzyl magnesium chloride (0.575 mmol) in THF:diethyl provides, after dehydration, 30.0 mg (44%) of the title compound as a 3:1 mixture of E- and Z-isomers. 1H NMR (CDCl3) δ 2.88-3.40 (m, 4 H), 6.26 (d, J=4.8 Hz, 1/4 H), 6.50 (d, J=8.2 Hz, 3/4 H); 6.63 (s, 1/4 H, Z), 6.74 (s, 3/4 H), 6.76 (td, J=8.6 Hz, 2.0 Hz, 3/4 H), 6.88 (td, J=8.2 Hz, 1.2 Hz, 3/4 H), 6.96 (s, 3/4 H), 6.95-6.98 (m, 1/4 H), 7.06 (d, J=4.8 Hz, 3/4 H), 7.08-7.20 (m, 14/4 H), 7.28 (d, J=2.0 Hz, 3/4 H), 7.34 (d, J=2.4 Hz, 1/4 H), 7.35-7.38 (m, 1/4 H); TLC shows 0.95% purity: Rf=0.20 (hexanes).

後処理

  1. customdiethyl provides

出典と根拠

ORDレコード
ord-c3183274c89d45a7b3b589a2ca8fae2a
出典データセット
uspto-grants-2008_08
特許番号
US07411072B2

関連ノート

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