Hydrochloric Acid → (R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-iodo-cyclopent-2-enone
Reaction equation
[I:1]I.N1C=CC=CC=1.[Si:9]([O:16][C@@H:17]1[CH2:21][C:20](=[O:22])[CH:19]=[CH:18]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].Cl>C(Cl)Cl>[Si:9]([O:16][C@@H:17]1[CH2:21][C:20](=[O:22])[C:19]([I:1])=[CH:18]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]Participants
Procedure
The procedure described in Johnson, C. R., Braun, M. P. J. Am. Chem Soc. 1993, 115, 11014 was followed with modification. A solution of I2 (6.55 g, 25.8 mmol) and pyridine (12 mL) in CH2Cl2 (12 mL) was cannula transferred to a 0° C. solution of (R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone (3.17 g, 14.9 mmol) and pyridine (5.4 mL) in CH2Cl2 (5.4 mL). The reaction was allowed to warm to room temperature and after 2 h, 100 mL 1 M HCl was added. The resulting mixture was extracted with CH2Cl2 (3×60 mL) and the combined organic solution was washed with 100 mL saturated NaHSO3 solution and 50 mL brine and then was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (ethyl acetate/hexanes) gave the title compound (4.997 g, 99%).
Workup
- customtransferred to a 0° C.
- extractionThe resulting mixture was extracted with CH2Cl2 (3×60 mL)
- washthe combined organic solution was washed with 100 mL saturated NaHSO3 solution and 50 mL brine
- dry with materialwas dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customPurification by flash chromatography (ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-6d33a35f21de4fbca5d7bce63f42ed93
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394273B2
Reaction notes
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