[OH:1][CH2:2][C:3](=[CH2:7])[C:4]([O-:6])=[O:5].[Li+].Cl.N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C=O)C>[Si:15]([O:1][CH2:2][C:3](=[CH2:7])[C:4]([OH:6])=[O:5])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]To lithium 2-(hydroxymethyl)prop-2-enoate (926 mg, 8.57 mmol) was added DMF (17.0 mL), HCl (1.07 mL, 4 M in dioxanes, 4.28 mmol) and imidazole (700 mg, 10.3 mmol), followed by TBS-Cl (2.84 g, 18.9 mmol) at 25° C. The reaction was stirred overnight, then quenched by pouring into a separatory funnel containing water. The aqueous layer was brought to pH˜3 with 1 N HCl and was extracted with ethyl acetate (×3). The organic layers were combined and dried with Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by chromatography using MPLC using 5-80% EtOAc/hexanes. The monoprotected product was collected and concentrated in vacuo to afford a clear oil. 1H NMR (600 MHz, DMSO-D6) δ 12.67 (s, 1H), 6.13 (s, 1H), 5.80 (s, 1H), 4.31 (s, 2H), 0.92 (s, 9H), 0.09 (s, 6H).
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