Table 3. In(OTf)₃ Mediated Etherification Reactions of Cinnamyl Alcohol in the Presence of Acetals and Ketals^a.

entry	acetal(equiv)	catalyst(mol %)	solvent	temp(°C)	ratio 2:3(%)b	yield 2 + 3(%)c	conversion(%)d
1	BDMA (1)	0.5	chloroform	rt		<10	<10
2	BDMA (1)	1.0	chloroform	rt	50:50	47	78
3	BDMA (1)	5.0	chloroform	rt	50:50	44	75
4	BDMA (3)	5.0	chloroform	rt	50:50	54	93
5	BDMA (1)	1.0	chloroform	rt → 60	100:00	67e	>95
6	DMOP (1)	0.5	chloroform	rt	35:65	23	50
7	DMOP (1)	1.0	chloroform	rt	50:50	60	>95
8	DMOP (1)	5.0	chloroform	rt	50:50	62	>95
9	DMOP (1)	1.0	chloroform	rt → 60	95:05	72e	>95
10	DMOP (3)	5.0	chloroform	rt	50:50	80	>95
11	DMOP (3)	5.0	acetone	rt	65:35	84	>95
12	DEOP (3)	5.0	acetone	rt	60:40	88	>95

^aExperimental conditions: In(OTf)₃ was added to a solution of 1 (0.5 mmol) and the specified acetal in chloroform (2 mL).

^bDetermined by ¹H NMR spectroscopy and GC–MS analysis of the crude reaction mixture.

^cCombined yield of ether products 2 and 3 as determined by quantitative ¹H NMR spectroscopy of the crude reaction mixture.

^dBalance of material is symmetrical ether 4.

^eHeated to 60 °C on completion of reaction for 15 min.