PENT-4-YNAL (IN DCM 30% W/W) synthesis
- Product Name:PENT-4-YNAL (IN DCM 30% W/W)
- CAS Number:18498-59-4
- Molecular formula:C5H6O
- Molecular Weight:82.1
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Yield: 7.18 g (92%)
Reaction Conditions:
with triethylamine in dichloromethane;water;dimethyl sulfoxide
Steps:
I Example I
Example I Pent-4-ynal. To a solution of oxalyl chloride (9.12 mL, 104.6 mmol) dissolved in methylene chloride (200 mL) at -78° C. was added dimethylsulfoxide (14.8 mL, 209.2 mmol) dissolved in methylene chloride (40 mL) over 20 minutes. The reaction solution was kept under a positive pressure of argon until workup. The reaction mixture was stirred for an additional 30 minutes when pent-4-yn-1-ol (8.00 g, 95.1 mmol) dissolved in methylene chloride (80 mL) was added over 10 minutes. Stirring was continued for an additional 60 minutes. Triethylamine (66.2 mL, 475.5 mmol) was added at -78° C. and the reaction mixture was stirred for 60 minutes and then allowed to warm to 10° C. over an additional hour. Water (200 mL) was added and the two layers were separated. The aqueous layer was acidified with 1% aqueous hydrochloric acid (saturated with NaCl) and then back-extracted with additional methylene chloride (3*100 mL). The combined organic layers were washed with 1% hydrochloric acid (in saturated brine solution, 6*100 mL) and 5% sodium bicarbonate solution (2*50 mL). The aqueous extracts were back-extracted with methylene chloride (2*100 mL) and the combined organic extracts were washed with brine (2*50 mL) and dried (MgSO4). The solvent was removed by rotary evaporation (30° C. water bath) to give 7.18 g (92%) of pent-4-ynal as a yellow oil. 1 H NMR (CDCl3): δ9.8 (s, 1H), 2.8-2.3 (m, 4H), 2.0-1.9 (t, 1H); 1R (neat): 3296 (s), 2926, 2848, 1725(s) cm-1; TLC (silica gel, 90% hexane: 10% ethyl acetate) Rf=0.43. 2-(But-3-ynyl)-1,3-dithiane.
References:
Marion Laboratories, Inc. US4877779, 1989, A
5390-04-5
288 suppliers
$13.00/1g
18498-59-4
25 suppliers
$45.00/10mg
79-37-8
474 suppliers
$17.67/10gm:
5390-04-5
288 suppliers
$13.00/1g
18498-59-4
25 suppliers
$45.00/10mg
181878-28-4
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18498-59-4
25 suppliers
$45.00/10mg
5390-04-5
288 suppliers
$13.00/1g
121-44-8
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$9.00/5g
18498-59-4
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$45.00/10mg