4-methoxy-3-methylsulfanylphenol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Hydroxy-1,3-benzoxathiol-2-one (2g, 11.9 mmol) [prepared according to J. Org. Chem. 1990, 55, 2736] was dissolved in acetone (13 mL) and treated with potassium carbonate (3.29 g, 23.8 mmol) followed by allyl bromide (1.13 mL, 13.1 mmol). The mixture was then stirred under nitrogen atmosphere for 24 hours. The reaction mixture was evaporated to dryness and the residue was partitioned between water and diethyl ether (50 mL each). The organic fraction was separated and the aqueous layer re-extracted with diethyl ether (50 mL). The combined organic fractions were dried (MgSO4) and evaporated to a brown oil. Purification by flash chromatography [SiO2; pentane/ ethyl acetate (95:5→90:10)] afforded the desired compound as a colourless oil (1.9 g, 77%); δH(CDCI3, 400 MHz) 4.50 (2 H, d), 5.28 (1 H, d), 5.38 (1 H, d), 6.00 (1 H, ddt), 6.83 (1 H, dd), 6.91 (1 H. d), 7.15 (1 H, d) The reaction mixture was evaporated to dryness the residue was partitioned between water and diethyl ether (50 mL each) The organic fraction was separated the aqueous layer re-extracted with diethyl ether (50 mL) The combined organic fractions were dried (MgSO4) evaporated to a brown oil Purification by flash chromatography [SiO2; pentane/ ethyl acetate (95:5→90:10)]

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Hydroxy-1,3-benzoxathiol-2-one (2 g, 11.9 mmol) [prepared according to J. Org. Chem. 1990, 55, 27361] was dissolved in acetone (13 mL) and treated with potassium carbonate (3.29 g, 23.8 mmol) followed by allyl bromide (1.13 mL, 13.1 mmol). The mixture was then stirred under nitrogen atmosphere for 24 h. The reaction mixture was evaporated to dryness and the residue was partitioned between water and diethyl ether (50 mL each). The organic fraction was separated and the aqueous layer was re-extracted with diethyl ether (50 mL). The combined organic fractions were dried (MgSO4) and evaporated to a brown oil. Purification by flash chromatography [SiO2; pentane/EtOAc (95:5→90:10)] afforded the desired compound as a colourless oil (1.9 g, 77%); δH (CDCl3, 400 MHz) 4.50 (2H, d), 5.28 (1H, d), 5.38 (1H, d), 6.00 (1H, ddt), 6.83 (1H, dd), 6.91 (1H, d), 7.15 (1H, d). The reaction mixture was evaporated to dryness the residue was partitioned between water and diethyl ether (50 mL each) The organic fraction was separated the aqueous layer was re-extracted with diethyl ether (50 mL) The combined organic fractions were dried (MgSO4) evaporated to a brown oil Purification by flash chromatography [SiO2; pentane/EtOAc (95:5→90:10)]