18-Crown-6

Other Names:

1,4,7,10,13,16-Hexaoxacyclooctadecane

General Information:

Structure:

CAS Number: 17455-13-9

Molecular Weight: 264.315 g/mol

Appearance: White solid

Melting Point: 42-45 C

Common Uses:

Ligand for certain cations (K+, Na+, etc.) in substitution reactions (ex. iodo substitution)

Procedure excerpt:

NaH (49.9 mg, 1.247 mmol) was added to a suspension of the SM (200 mg, 0.831 mmol) and 18-crown-6 (10.39 mg, 0.042 mmol) in THF (14 mL) and DMSO (2 mL) at 0 C. The mixture . . .

[full procedure]

Ligand for certain cations (K+, Na+, etc.) in substitution reactions (ex. tosylate substitution)

Procedure excerpt:

. . . the alcohol (200 mg, 0.524 mmol), K2CO3 (146 mg, 1.06 mmol), and ACN (7 mL) was added the tosylate (126 mg, 0.577 mmol) and 18-Crown-6 (28.6 mg, 0.105 mmol). The reaction . . .

[full procedure]

Ligand for certain cations (K+, Na+, etc.) in substitution reactions (ex. mesylate substitution)

Procedure excerpt:

To a solution of the SM (14.0 g, 40.6 mmol) in DMF (150 mL) at 0 C was added 18-Crown-6 (550 mg) and NaCN (5.3 g, 81.0 mmol). The reaction was stirred at RT for 16 h, after . . .

[full procedure]

References:

1) Patent Reference: WO2016011930, page 117, (15.7 MB)

2) Patent Reference: WO2014177977, page 66, (6.0 MB)

3) Patent Reference: WO2014149164, page 234, (23.7 MB)

4) Wikipedia: 18-Crown-6 (link)

5) www.sigmaaldrich.com: 18-Crown-6 (link)