C[S:2][P:3]([O-:6])[O:4][CH3:5].[C:7]([O:11][C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br)([CH3:10])([CH3:9])[CH3:8].[OH-].[Na+].Cl[CH2:23]Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[C:7]([O:11][C:12](=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][P:3]([O:6][CH3:23])([O:4][CH3:5])=[S:2])([CH3:10])([CH3:9])[CH3:8]A solution of dimethylthiophosphite (4.56 g, 36.2 mmol), 6-bromohexanoic acid tert-butyl ester (100 g, 39.8 mmol) and triethylbenzylammonium chloride (0.82 g, 3.62 mmol) in dichloromethane (100 mL) was cooled on an ice bath and a solution of sodium hydroxide (14.5 g, 0.362 mol) in water (14.5 mL) was added slowly with vigorous stirring. The ice bath was removed and the mixture stirred for 3 days before being washed with water, dried (magnesium sulfate), and the solvent removed under reduced pressure to give crude 6-(dimethoxythiophosphoryl)hexanoic acid tert-butyl ester (8.00 g).
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