1-cyclopropylprop-2-yn-1-ol synthesis
- Product Name:1-cyclopropylprop-2-yn-1-ol
- CAS Number:1656-85-5
- Molecular formula:C6H8O
- Molecular Weight:96.13
1489-69-6
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4301-14-8
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Yield:1656-85-5 90%
Reaction Conditions:
in tetrahydrofuran at 0; for 3 h;
Steps:
103 4-Cyclopropyl-7-methyl-5-(4-(trifluoromethyl)phenylsulfonyl)-4,5-dihydro-1H-pyrazolo[3,4-d]thiazolo[5,4-b]pyridine (149)
To a solution of aldehyde 138 (5.00 g, 71.3 mmol) in THE (50 mL) at 0° C. was added ethynylmagnesium bromide (139) (0.5M in THF, 178 mL, 89.2 mmol), dropwise via a pressure equalizing addition funnel. The reaction mixture was stirred for 3 h at 0° C., and then quenched with saturated aqueous NH4Cl (100 mL) and warmed to room temperature. The reaction mixture was filtered through a pad of Celite. The filtrate was diluted with EtOAc (100 mL) and the layers were separated. The organic layer was washed with saturated aqueous NaCl (100 mL), dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (20% EtOAc in hexanes) to afford 6.15 g of alcohol 140 (90%). 1H NMR (300 MHz, CDCl3) δ 4.20 (bd, J=5.6 Hz, 1H), 2.44 (d, J=2.1 Hz, 1H), 1.90 (bs, 1H), 1.25 (m, 1H), 0.57 (m, 2H), 0.52 (m, 2H).
References:
US2008/21056,2008,A1 Location in patent:Page/Page column 106; 107
192315-00-7
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65032-27-1
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1489-69-6
325 suppliers
$6.00/1g
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