Acetonitrile → HCID 59649717、化合物

温度

100 °C

Argon was bubbled into a mixture of the 4-iodo-2-methoxymethoxy-1-methyl-benzene (7.63 g, 27.5 mmol) (from example 18 supra), triethylamine (55 mL) (Aldrich) and acetonitrile (100 mL) in a pressure reactor for 20 minutes at room temperature. Ethynyltrimethylsilane (9.2 mL, 64.5 mmol) (Aldrich), copper(I) iodide (245 mg, 1.28 mmol) (Aldrich) and dichlorobis(triphenylphosphine)palladium(II) (911 mg, 1.29 mmol) (Aldrich) were added. Reactor was capped and mixture heated at 100° C. for 5 hours with magnetic stirring. After cooling to room temperature, mixture was suspended in diethyl ether (250 mL) and water (250 mL) and filtered through Celite®. Layers were separated. Organic layer washed with water (250 mL) and brine (250 mL). Aqueous layers were back washed with ether (250 mL). Organic layers were combined, dried (MgSO4), filtered and concentrated. Residue was dissolved in methanol (50 mL) and potassium carbonate (500 mg) was added. Mixture was stirred at room temperature overnight. After concentrating, residue was partitioned between diethyl ether (2×250 mL) and water (2×250 mL). Organic layers were washed with brine (200 mL), combined, dried (MgSO4), filtered and concentrated. Residue was purified by flash chromatography (Biotage 40 L, hexanes, then hexanes-dichloromethane 9:1 and 3:1 as solvent) to give 4-ethynyl-2-methoxymethoxy-1-methyl-benzene as a brown oil. (Yield 4.65 g, 96.2%).

1. customReactor was capped
2. temperatureAfter cooling to room temperature
3. filtrationwater (250 mL) and filtered through Celite®
4. customLayers were separated
5. washOrganic layer washed with water (250 mL) and brine (250 mL)
6. washAqueous layers were back washed with ether (250 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. dissolutionResidue was dissolved in methanol (50 mL)
11. additionpotassium carbonate (500 mg) was added
12. concentrationAfter concentrating
13. customresidue was partitioned between diethyl ether (2×250 mL) and water (2×250 mL)
14. washOrganic layers were washed with brine (200 mL)
15. dry with materialdried (MgSO4)
16. filtrationfiltered
17. concentrationconcentrated
18. customResidue was purified by flash chromatography (Biotage 40 L, hexanes

ORDレコード

ord-7fa827fb744e4bb5a7966b70d4f4299e

出典データセット

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07932390B2