ChemicalBook CAS DataBase List 5-PHENYL-1-PENTYNE

5-PHENYL-1-PENTYNE synthesis

9synthesis methods

Product Name:5-PHENYL-1-PENTYNE
CAS Number:1823-14-9
Molecular formula:C11H12
Molecular Weight:144.21

Benzene, [5-(trimethylsilyl)-4-pentyn-1-yl]-

110211-35-3
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1823-14-9
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Yield:1823-14-9 57.02%

Reaction Conditions:

with tetrabutyl ammonium fluoride in tetrahydrofuran at 20; for 1 h;

Steps:

45B Preparation of compound C1348-H.
To a solution of C1348-G (25 g, 115.53 mmol, 1 eq) in THF (50 mL) was added tetra-n-butylammonium fluoride (TBAF) (1 M, 150.19 mL, 1.3 eq). The mixture was stirred at 20°C for 1hr to give a yellow solution. TLC (eluting with: PE/EtOAc=10/1) showed the reaction was complete. The reaction mixture was quenched with H₂O (300 mL) and extracted with EtOAc (150 x 3). The organic layers were dried over Na₂SO₄ and concentrated to give the crude product. The crude product was purified by a flash column (eluting with: PE/EtOAc=100%PE to 5%) to give C1348-H (9.5 g, 65.88 mmol, 57.02% yield) as a colorless oil. ¹H NMR (400MHz, CDCl₃): δ 7.32-7.13 (m, 5H), 2.74-2.65 (m, 2H), 2.14-2.11 (m, 5H), 1.93 (s, 1H), 1.80-1.67 (m, 2H).

References:

K-GEN, INC. WO2021/62030, 2021, A1 Location in patent:Paragraph 0491; 0495; 0496

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637-59-2 Synthesis