Propionyl chloride → HCID 11357456, compound

Participants

Reaction Steps

Reaction of the auxiliary (10) (0.8 g, 3.90 mmol) in solution in tetrahydrofuran (27 ml) at -78° C. with butyllithium (1.3M, 3.03 ml, 3.94 mmol) and propionyl chloride (0.373 ml, 4.29 mmol) for 30 minutes and then at room temperature overnight with work-up and recrystallisation from pentane gave the title compound (20) as a solid (0.870 g, 85%); mp 61° C.; νmax (CHCl3) 1773 and 1702 cm-1 ; [α]D25 (c 1 in CHCl3)=-42.5; (Found: C, 69.06; H, 7.43; N, 5.21. C15H19NO3 requires C, 68.94; H, 7.33; N, 5.36%); δH (CDCl3 ; 200 MHz) 1.13 (3H, t, J=7.36, CH2CH3), 1.35 (3H, s, C(CH3)2), 1.36 (3H, s, C(CH3)2), 2.81-2.98 (2H, m, CH2Ph and CH2CH3), 3.14 (1H, dd, J=4.0 and 14.4, CH2Ph), 4.50 (1H, dd, J=4.0 and 9.6, CHCH2), 7.18-7.34 (5H, m, ArCH); δC (125 MHz; CDCl3) 8.20 (CH3), 22.15 (CH3), 28.43 (CH3), 29.23 (CH2), 35.24 (CH2), 63.46 (CH), 82.20 (C), 126.96 (CH), 128.82 (CH), 129.26 (CH), 137.26 (C), 152.93 (CO), 174.53 (CO); m/z (CI+, NH3) 262 (M+ +1).

Provenance & Evidence