4-Toluenesulfonyl chloride → HCID 15478441, compound
Reaction equation
[C:1]1([C:7]#[C:8][CH2:9]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[OH-].[K+]>>[S:17]([CH2:9][C:8]#[C:7][C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1)([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18]Participants
4
Procedure
3-cyclohexenyl-2-propyn-1-ol (95)(3.04 g, 22.3 mmol), p-toluene sulfonyl chloride (4.04 g, 21.2 mmol) and potassium hydroxide (6.26 g, 112 mmol) were reacted using the above procedure to yield the product (5.66 g, 19.5 mmol, 91.8%) as a light yellow oil. 1H NMR (CDCl3): 7.79 (d, J=8.1 Hz, 2 H), 7.31 (d, J=8.1 Hz, 2 H), 5.97 (m, 1 H), 4.81 (s, 2 H), 2.42 (s, 3 H), 2.02 (m, 2 H), 1.92 (m, 2 H), 1.53 (m, 4 H). FAB LRMS (m/e): calcd. for (MH+)(C16H19O3S): 29 1, found 29 1.