3-Bromo-1-propanol → HCID 11697277, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(3,5-dimethyl-4-hydroxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (3.00 g, 8.46 mmol, Intermediate 10) in isopropanol (80 mL) and 2 N aq. NaOH (30 mL) is treated with 3-bromopropanol (2.35 g, 16.9 mmol). The dark red reaction mixture is stirred at 70° C. for 5 h. The solvent is removed under reduced pressure and the residue is dissolved in EA and washed twice with water. The organic layer is dried over MgSO4 and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 1:1 to give 3-[4-(3-hydroxy-propoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-tri methyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (2.55 g) as a yellow oil; LC-MS: tR=1.10 min, [M+1]+=413.33; 1H NMR (CDCl3): δ 6.87 (s, 2H), 3.99-3.90 (m, 4H), 3.04-2.85 (m, 5H), 2.81 (d, J=18.8 Hz, 1H), 2.39 (s, 3H), 2.27 (s, 6H), 2.10-2.01 (m, 2H), 1.93-1.88 (m, 2H), 1.13 (s, 3H), 0.72 (s, 3H).

Provenance & Evidence