Lab work presentation By: Yeersen Patehebieke
1. Nitration of 1 -bromo-3 -phenyl propane Yield=67% 2. Preparation of β-nitro alcohol via nitro aldol condensation reaction Entry Ethyl glyoxylate Solvent(ml /mmol) Base Am-21 (mg/mmol) Time Yield 1 1. 2 eq 10 ml/mmol 200 mg/mmol 16 h 43. 97% 2 1. 2 eq 1 ml/mmol 200 mg/mmol 16 h 66. 1%
3. Acidic esterification Entry Ac 2 O Solvent(ml /mmol) Acid Am-15 (mg/mmol) Time Yield 1 1. 2 eq Sol. FC 25 mg/mmol 2 h 94. 5% 2 1. 3 eq Sol. FC 25 mg/mmol 2 h Quantitative 4. Base induced elimination of acidic acid to form β-nitroacrylate Entry Solvent(ml /mmol) Base (eq) Time Yield 1 Et. OAc (0. 6 ml/mmol) KF-Al 2 O 3 (1. 1) 20 h 82. 8% 2 Et. OAc (0. 6 ml/mmol) KF-Al 2 O 3 (1. 1) 22 h 81%
5. Micheal addition and β-elimination to form thioester pentenoate
6. Hydrolysis of thioacetate ester Entry Solvent Acid/Base (equivalent) Condition Temperature() Time Yield 1 Me. CN Na. OH (1. 5) microwave 100 2 h —— 2 Me. CN Ts. OH. H 20 (2) microwave 130 4 h —— 3 Me. CN Ts. OH. H 20 (4) microwave 130 4 h 38% 4 Me. CN H 3 PO 4 (4) microwave 130 2 h —— 5 Me. CN Ts. OH. H 20 (5) microwave 130 2 h 17. 6% 6 Me. CN Ts. OH. H 20 (5) microwave 100 3. 5 h 41. 9% 7 Et 0 H HCl 4 N/water (10) batch r. t 4 h —— 8 Me. OH K 2 CO 3 (0. 75) batch 1 h ice cooling, 2 h r. t 3 h 32. 8%
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