9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-one → 4-(3,5-Dimethyl-benzylidene)-9,10-dihydro-4H-1-thia-benzo[f]azulene

HRID 2218725Notes

Reaction equation

HRID 2218725 reaction equation
[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.[CH3:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([CH3:26])[CH:25]=1)[CH2:20][Mg]Br>C1COCC1>[CH3:16][C:17]1[CH:25]=[C:24]([CH:23]=[C:19]([CH3:20])[CH:18]=1)[CH:26]=[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

Participants

4

Reactant 2

HCID 7684929,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-oneHCID 178424986HCID 178424986, compound

Product 1

HCID 689383664-(3,5-Dimethyl-benzylidene)-9,10-dihydro-4H-1-thia-benzo[f]azuleneYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedures essentially as described in Example 238 and using 9,10-dihydro-1-thia-benzo[f]azulene-4-one (47.0 mg (0.22 mmol) and solution of 3,5-dimethylbenzyl magnesium bromide(0.650 mmol) in THF, provides, after dehydration, 39.6 mg (57%) of the title compound as a 1.6:1 mixture of E- and Z-isomers. MS (EI): 316 (M+); 1H NMR (CDCl3) δ 2.13 (s, 18/5 H), 2.24 (s, 12/5 H), 2.40-3.80 (m, 4 H), 6.54 (d, J=5.6 Hz, 2/5 H), 6.53-6.55 (m, 7/5 H), 6.74 (s, 3/5 H), 6.83-6.84 (m, 2/5 H), 6.86 (s, 3/5 H), 6.93 (s, 3/5 H), 7.01-7.02 (m, 1 H), 7.08 (app d, J=5.6 Hz, 2/5 H), 7.14 (app d, J=5.6 Hz, 2/5 H), 7.19-7.25 (m, 4 H), 7.30 (d, J=8.0 Hz, 3/5 H), 7.37-7.39 (m, 2/5 H).

Workup

  1. customprovides

Sources & evidence

ORD record
ord-d4c761dd419b49ebb1e50581ec37c4a2
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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