Phenylacetylene → 5-tert-Butyl-2-phenyl-benzo[b]furan
Reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15](I)[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>>[C:9]([C:13]1[CH:18]=[CH:17][C:16]2[O:19][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:15]=2[CH:14]=1)([CH3:12])([CH3:11])[CH3:10]Participants
3
Procedure
The general procedure was used to convert phenylacetylene and 4-tert-Butyl-2-iodophenol to the title product. Purification by flash chromatography (10% ethyl acetate in hexanes as the eluent) gave the analytically pure product as a white solid (398 mg, 80% yield). 1H NMR (300 MHz, CDCl3) δ 7.83 (dd, J=7.16, 2H), 7.57-7.56 (m, 1H), 7.44-7.38 (m, 3H), 7.34-7.30 (m, 2H), 6.96 (s, 1H), 1.38 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 155.99, 153.12, 145.92, 130.65, 128.88, 128.72, 128.33, 124.82, 122.23, 117.06, 110.42, 101.48, 34.68, 31.83. Anal. Calcd. for C18H18O: C, 86.36; H, 7.25. Found C, 86.34; H, 7.13. m.p.: 103-104° C. (lit., 7102-103° C.).
Sources & evidence
- ORD record
- ord-42dea26e9d64418495f07ef3c8b3c62a
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473786B1
Reaction notes
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