[SH:1][CH2:2][CH2:3][OH:4].[N+:5]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1)([O-:7])=[O:6].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.C1OCCOCCOCCOCCOCCOC1>[N+:5]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12][S:1][CH2:2][CH2:3][OH:4])=[CH:10][CH:9]=1)([O-:7])=[O:6]β-Mercaptoethanol (3.3 mL, 47.2 mmol) was added to a suspension of 4-nitrobenzyl bromide (10.0 g, 46.3 mmol), K2CO3 (16.1 g, 116.5 mmol), KI (154 mg, 0.9 mmol), and 18-crown-6 (258 mg, 1.0 mmol) in acetone (105 mL). The mixture was refluxed under N2 for 1.5 h, cooled to room temperature, filtered through a pad of celite, and concentrated in vacuo. The filtrate was poured into water (100 mL) and extracted with Et2O (2×100 mL). The extracts were washed with brine (150 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give an orange oil (11.78 g), which was used in the following step without purification. MS: M(C9H11NO3S)=213.26, (M−OH)+=196.0.
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