2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate → 4-[2-(Benzo[b]thiophen-7-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

HRID 479166Notes

Reaction equation

HRID 479166 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([OH:10])[C:2]1=2.[CH3:11][C:12]1[O:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:13]=1[CH2:23][CH2:24]OS(C)(=O)=O>>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH2:24][CH2:23][C:13]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[O:16][C:12]=3[CH3:11])[C:2]1=2

Participants

3

Reactant 2

HCID 105407732-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonateHCID 110840501-Benzothiophen-7-ol

Product 1

HCID 180035774-[2-(Benzo[b]thiophen-7-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

Procedure

In analogy to the procedures described in example 91 a] and b], benzo[b]thiophen-7-ol [J. Chem. Soc., Perkin Trans. 1 (1983), (12), 2973-7] was reacted with methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester [PCT Int. Appl. (2000) WO0008002]) to yield 4-[2-(benzo[b]thiophen-7-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole. Treatment of 4-[2-(benzo[b]thiophen-7-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole with dichloromethyl methyl ether and titanium tetrachloride then gave 7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-4-carbaldehyde as a yellow solid. NMR: (CDCl3, 1H, δ, TMS, 300 MHz) 2.45 (s, 3H), 3.12 (t, J=6, 2H), 4.55 (t, J=6, 2H), 6.92 (d, J=8, 1H), 7.39-7.46 (m, 3H), 7.66 (d, J=5, 1H), 7.80 (d, J=8, 1H), 7.95-7.99 (m, 2H), 8.35 (d, J=5, 1H), 10.1 (s, 1H).

Sources & evidence

ORD record
ord-b1542880d042425781a388fe183fe658
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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