ChemicalBook CAS DataBase List 4-PHENYL-3-BUTYN-1-OL

4-PHENYL-3-BUTYN-1-OL synthesis

10synthesis methods

Product Name:4-PHENYL-3-BUTYN-1-OL
CAS Number:10229-11-5
Molecular formula:C10H10O
Molecular Weight:146.19

591-50-4 Synthesis

591-50-4
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927-74-2 Synthesis

927-74-2
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10229-11-5
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Yield: 100%

Reaction Conditions:

with copper(l) iodide;tetrakis(triphenylphosphine) palladium⁽⁰⁾;triethylamine for 16 h;Reflux;Inert atmosphere;Schlenk technique;Sonogashira Cross-Coupling;

Steps:

4-Phenylbut-3-yn-1-ol (17a)
Iodobenzene (16a, 0.20 mL, 1.83 mmol, 1 eq) was dissolved under N₂ atmosphere in triethylamine (20 mL). CuI (7.0 mg, 0.04 mmol, 0.02 eq), Pd(PPh₃)₄ (63.4 mg, 0.05 mmol, 0.03 eq) and but-3-yn-1-ol (7, 0.20 mL, 2.71 mmol, 1.48 eq.) were added and the solution was heated to reflux for 16 h. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (d = 2 cm, h = 15 cm, V = 10 mL, cyclohexane:ethyl acetate = 2:1 ). Orange oil, yield 267 mg (1.83 mmol, 100 %). C₁₀H₁₀O (146.2). R_f = 0.35 (cyclohexane:ethyl acetate = 2:1). HPLC: 97.5 %, t_R = 17.18 min. ¹H NMR (400 MHz, CDCl₃): δ [ppm] = 1.79 - 1.95 (m, 1H, OH), 2.70 (t, J = 6.3 Hz, 2H, PhCCCH₂CH₂OH), 3.82 (t, J = 6.3 Hz, 2H, PhCCCH₂CH₂OH), 7.27 - 7.45 (m, 5H, phenyl). ¹³C NMR (101 MHz, CDCl₃): δ [ppm] = 24.0 (1C, PhCCCH₂CH₂OH), 61.3 (1C, PhCCCH₂CH₂OH), 82.6 (1C, PhCCCH₂CH₂OH), 86.5 (1C, PhCCCH₂CH₂OH), 123.5 (1C, C-1_phenyl), 128.1, 128.4, 131.8 (5C, C-2_phenyl, C-3_phenyl, C-4_phenyl, C-5_phenyl and C-6_phenyl). IR: v[cm^-1] = 3364 (O-H), 3032 (=C-H), 2932, 2886 (C-H_aliph.), 1678, 1597, 1489 (C=C_arom.), 1443 (CH₂deform.), 1042 (C-OH). Exact Mass (APCI): m/z = 147.0804 (calcd. 147.0806 for C₁₀H₁₁O [MH]⁺).

References:

Wagner, Marina;Schepmann, Dirk;Ametamey, Simon M.;Wünsch, Bernhard [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 16,p. 3559 - 3567] Location in patent:supporting information

108-86-1 Synthesis