Ethyl vanillate → Ethyl 3-methoxy-4-(naphth-2-ylmethoxy)benzoate
Reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C:13]([O:24][CH2:25][CH3:26])(=[O:23])[C:14]1[CH:22]=[CH:21][C:19]([OH:20])=[C:16]([O:17][CH3:18])[CH:15]=1>>[CH3:18][O:17][C:16]1[CH:15]=[C:14]([CH:22]=[CH:21][C:19]=1[O:20][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)[C:13]([O:24][CH2:25][CH3:26])=[O:23]Participants
3
Procedure
2-Bromomethylnaphthalene was reacted with ethyl vanillate using the conditions described in Example 1 to give ethyl 3-methoxy-4-(naphth-2-ylmethoxy)benzoate in 54% yield, m.p. 86°-87° C. Following the procedures described in the portion of Example 6 which is concerned with the preparation of starting materials the product so obtained was reacted with thiazol-2-yl-lithium and the resultant product was reacted with ethylmagnesium iodide to give the required starting material as an oil in 20% yield, m.p. 124°-126° C. (recrystallised from a mixture of hexane and ethyl acetate).
Sources & evidence
- ORD record
- ord-0014cb0ede0440a2aae2dd3229a51e46
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05089513
Reaction notes
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