potassium hydroxide in ethanol; water 1.5 h; Heating;

1: With benzo[1,3,2]dioxaborole T=60°C; 5 h; 2: With acetic acid-d1; acetic acid 5 h; Heating; 3: With potassium hydroxide in water 1 h; Heating; Further stages. Title compound not separated from byproducts.;

1: 1) EtMgBr / 1) ether, 1h, reflux, 2) 30 min, reflux 2: 63 percent / PBr3, pyridine / diethyl ether / 3 h / Heating 3: 1) EtMgBr, 2) CuCN / 1) THF, RT, 2h, 2) THF, 23h, reflux 4: 95 percent / diethyl ether / 0 °C 5: 53 percent / NaBD4, 2-methylbut-2-ene, BF3*OEt2 / bis-(2-methoxy-ethyl) ether / 1) 0 deg C, 30 min, 2) RT, 2h 6: 70 percent / KOH / ethanol; H2O / 1.5 h / Heating View Scheme

1: 1) EtMgBr, 2) CuCN / 1) THF, RT, 2h, 2) THF, 23h, reflux 2: 95 percent / diethyl ether / 0 °C 3: 53 percent / NaBD4, 2-methylbut-2-ene, BF3*OEt2 / bis-(2-methoxy-ethyl) ether / 1) 0 deg C, 30 min, 2) RT, 2h 4: 70 percent / KOH / ethanol; H2O / 1.5 h / Heating View Scheme

1: 63 percent / PBr3, pyridine / diethyl ether / 3 h / Heating 2: 1) EtMgBr, 2) CuCN / 1) THF, RT, 2h, 2) THF, 23h, reflux 3: 95 percent / diethyl ether / 0 °C 4: 53 percent / NaBD4, 2-methylbut-2-ene, BF3*OEt2 / bis-(2-methoxy-ethyl) ether / 1) 0 deg C, 30 min, 2) RT, 2h 5: 70 percent / KOH / ethanol; H2O / 1.5 h / Heating View Scheme

1: 95 percent / diethyl ether / 0 °C 2: 53 percent / NaBD4, 2-methylbut-2-ene, BF3*OEt2 / bis-(2-methoxy-ethyl) ether / 1) 0 deg C, 30 min, 2) RT, 2h 3: 70 percent / KOH / ethanol; H2O / 1.5 h / Heating View Scheme

1: 53 percent / NaBD4, 2-methylbut-2-ene, BF3*OEt2 / bis-(2-methoxy-ethyl) ether / 1) 0 deg C, 30 min, 2) RT, 2h 2: 70 percent / KOH / ethanol; H2O / 1.5 h / Heating View Scheme