Water → trans-2-(allyloxy)-1-azido-6-methoxy-2,3-dihydro-1H-indene

Participants

Reaction Steps

Step AA (5): To a solution of (1RS,2RS)-1-azido-6-methoxy-2,3-dihydro-1H-inden-2-ol (64 mg) from Step AA (4) in DMF (0.30 mL) at rt was added sodium hydride (95% purity, 20 mg), and the resulting mixture was stirred at rt for 5 min. Allyl bromide (40 μL) was added, and the reaction mixture was stirred for 5 min. Water was added, the aqueous layer was extracted with EtOAc (×3), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give trans-2-(allyloxy)-1-azido-6-methoxy-2,3-dihydro-1H-indene as a slightly yellowish oil (71 mg). 1H NMR (400 MHz, CDCl3) δ 7.09 (1H, d), 6.84 (2H, m), 5.96 (1H, m), 5.34 (1H, d), 5.23 (1H, d), 4.75 (1H, d), 4.23 (1H, q), 4.16 (2H, q), 3.80 (3H, s), 3.21 (1H, dd), 2.78 (1H, dd).

Provenance & Evidence