Hydrochloric Acid → HCID 86603001, compound

Participants

Reaction Steps

A solution of (S)-1-[2-((S)-1-Hydroxy-2-methylpropyl)phenyl]-2-methyl-propan-1-ol (1.0 g, 4.9 mmol) in pyridine (1.16 g 14.7 mmol) was cooled with an ice-bath. To this mixture was then added drop wise phenyl phosphonic acid dichloride (0.96 g, 4.9 mmol). After stirring for 90 minutes the reaction was complete by 31P-NMR. To the mixture was then added TBME (ca. 20 ml) and hydrochloric acid (ca. 5 ml 4N-solution). The organic layer was separated, dried (Na2SO4), and removal of the solvent left the product as an oil. Yield 1.50 g (89%). 1H/13C-NMR (CDCl3, HSQC/HMBC) δ/δ 0.965 (d, J=6.5 Hz)/20.38 (CH3); 1.075 (d, J=6.5 Hz)/19.05 (CH3); 1.106 (d, J=6.5 Hz)/17.71 (CH3); 1.112 (d, J=6.7 Hz)/20.38 (CH3); 2.37 (m)/34.58 (d, J=8.3 Hz) (CHMe2); 2.49 (m)/31.28 (d, J=7.6 Hz) (CHMe2); 5.17 (dd, J=5.6 Hz, J=7.6 Hz)/83.85 (d, J=8.9 Hz) (CH(i-Pr)); 5.53 (dd, J=3.8 Hz, J=5.9 Hz)/84.36 (d, J=7.6 Hz) (CH(i-Pr)); 7.24 (m)/127.28 (Ar CH); 7.24 (m)/127.93 (Ar CH); 7.24 (m)/127.95 (Ar CH); 7.27 (m)/128.31 (Ar CH); 7.37 (m)/128.43 (d, J=15.1 Hz) (Ph meta-CH); 129.12 (d, J=193 Hz) (Ph ipso-C); 7.47 (m)/132.38 (d, J=3.0 Hz) (Ph para-CH); 7.70 (m)/131.63 (d, J=9.8 Hz) (Ph ortho-CH); 137.23 (s), 138.48 (d, J=1.0 Hz) (2 Ar ipso-C). 31P-NMR (CDCl3) δ 18.72.

Provenance & Evidence