4-Toluenesulfonyl chloride → HCID 54383241, compound

Participants

Reaction Steps

The method followed that described in Example 9 but using (+)-(R)-1-(4-pyridyl)ethanol (1.84 g, 15.0 mmol) in THF (80 ml), butyllithium (1.6M; 9.4 ml, 15.0 mmol) in hexane, p-toluenesulfonyl chloride (2.86 g, 15.0 mmol), diisopropylamine (6.31 ml, 45.0 mmol) in THF (120 ml), butyllithium (1.6M; 28.12 ml, 45.0 mmol) in hexane and 1-adamantyl methyl ketone (8.0 g, 45 mmol). Chromatography, on elution with petrol-ether-triethylamine 100:50:1 gave the title compound (722 mg, 17%), which crystallised from hexane, m.p. 48°-49° C.; [α]D -6.6° (c 1.0, MeOH). IR, NMR and MS data were the same as given in Example 14.

Provenance & Evidence