[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=1[O:11][CH3:12])[CH2:6][OH:7].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH2:13][CH2:14][CH3:15])[C:10]=1[O:11][CH3:12])[CH2:6][O:7][S:24]([CH3:23])(=[O:26])=[O:25]To a stirred solution of 3,4-dimethoxy-5-propylbenzylalcohol (171 mg, 0.82 mmol) in CH2Cl2 (5.0 mL) at room temperature was added triethylamine (0.23 mL, 1.63 mmol) followed by methanesulfonyl chloride (95 μL, 1.22 mmol, 1.5 eq.). After 30 min the reaction mixture was diluted with hexanes (20 mL) and filtered through a pad of silica gel. The pad was then washed with 25% EtOAc in hexanes (100 mL). The combined organic filtrate was then concentrated to give methanesulfonic acid 3,4-dimethoxy-5-propylbenzyl ester (122 mg) as oil, which was used without further purification.
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