Question

Problem 8 synthetic intermediate OH O Онон 1 step 2 steps Spectral Data is given below for the intermediate in the three step synthesis shown above. Draw the structure of the synthetic intermediate. (It may be beneficial to look over chapter 11.6 in the textbook) Molecular Formula: C140 SiH30 Important IR peaks: narrow band at 1720 cm, NO broad peak spanning 3550 - 3200 cm H-NMR PPM 8: 9.72 (t, IH) 8: 3.72 (ddt, 1H) 8: 2.74 (sept, 3H) 8:2.40 (ddd, 2H) 8: 1.46 (pent, 2H) 8: 1.29 (d, 18H) 8: 0.89 (t, 3H)

Answer 1

problems 앤 요 MF = C140₂8 +4230 imidazole, o synthetic intermediate M9137 Oscy on TBAF de protech of silyl groun = In NMR spectrum values, & 1.29 (d, 18H) Indicates the prosence of 6 methyls (correspondsing to 18 Hydrogens (3 isopropyls) an addition to this septet at Q.7 for 3H's indicates that the bydooxyl group is protected cuils Tripsopropyl Silyl chloride .: Full Synthetic route follows as shown above on H104 osoa DOM 05044 di bydroxylation dial cleavage omgr 04 HBO pec pec oh oxidation