Triethylamine → 3-(3,4-Dimethoxyphenyl)propan-1-ol mesylate

HRID 1031792Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH2:16][CH2:17][CH2:18][OH:19])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2]([O:19][CH2:18][CH2:17][CH2:16][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:8]([O:7][CH3:6])[CH:9]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Under N2, methanesulfonyl chloride (129.7 g, 1.132 m, 87.6 cc) was added dropwise over 1-1.5 hours at -10° to 0° C. to a mechanically stirred solution of 3-(3,4-dimethoxyphenyl)-1-propanol (202 g, 1.03 mole) and Et3N (158.3 g, 1.56 mole, 218 cc) in CH2Cl2 (1.5 1) contained in a 5 1, 3-neck flask. The reaction mixture was stirred at 0° C. for 1 hour and then washed successively with icewater (1×700 cc), cold 3N HCl (1×700 cc), saturated NaHCO3 solution (1×700 cc) and brine (1×700 cc). The organic solution was dried (Na2SO4) and concentrated in vacuo to an orange syrup; yield: 282 g (100%).

Workup

washwashed successively with icewater (1×700 cc), cold 3N HCl (1×700 cc), saturated NaHCO3 solution (1×700 cc) and brine (1×700 cc)
dry with materialThe organic solution was dried (Na2SO4)
concentrationconcentrated in vacuo to an orange syrup

Sources & evidence

ORD record: ord-fc51bbd923c4403d99f7cf0b7e36aac6
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04954659

Reaction notes

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