9,10-Dihydro-3-thia-benzo[f]azulen-4-one → 4-(2,4-Dichloro-benzylidene)-9,10-dihydro-4H-3-thia-benzo[f]azulene

HRID 2218726노트

반응식

HRID 2218726 반응식
[CH: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[S: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[CH:1]=[CH:2][S:3][C:4]1=2

참가 물질

4

반응물 2

HCID 122331029,10-Dihydro-3-thia-benzo[f]azulen-4-oneHCID 178478998HCID 178478998, 화합물

생성물 1

HCID 689339824-(2,4-Dichloro-benzylidene)-9,10-dihydro-4H-3-thia-benzo[f]azulene수율 32.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Following the procedures essentially as described in Example 238 and using 9,10-dihydro-3-thia-benzo[f]azulene-4-one (23.3 mg, 0.108 mmol) and solution of 2,4-dichlorobenzyl magnesium chloride (0.325 mmol) in THF provides, after dehydration, 12.5 mg (32%) 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, 15/4 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 >95% purity: Rf=0.20 hexanes).

후처리

  1. customprovides

출처 및 근거

ORD 기록
ord-b307026f1a744e6ea3103ffa32f60e76
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07411072B2

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