C(OCC[CH2:7][CH2:8][CH2:9][N:10]=[N+:11]=[N-:12])(=O)C.[C:13]([O-:16])([O-])=O.[K+].[K+].[C:19]([O-])(=O)C.[K]>CO.O>[N:10]([CH:9]([CH3:19])[CH2:8][CH2:7][CH2:13][OH:16])=[N+:11]=[N-:12]5.1 g of 4-azido-1-pentylacetate (4.46) (33 mmol, 1.0 eq) from Example 19 was dissolved in 30 mL of MeOH and 2 mL of water. This solution was then saturated with K2CO3 and stirred overnight at room temperature. The reaction was then checked by TLC to confirm conversion of the acetate to the primary hydroxyl. Water (300 mL) was added to dissolve the potassium salt and extracted with diethyl ether 3×100 mL. The organic extracts were combined and dried with MgSO4. The solution was filtered and concentrated under vacuum with no external heat resulting in 4-azido-1-pentanol 4.47: 65% Yield; 1H NMR (500 MHz, Acetone-d6): δ: d 3.56 (t, J=4.2 Hz, 2H), 3.45 (t, J=7 Hz, 2H), 1.69-1.37 (m, 6H)13C NMR (100 MHz, Acetone): δ: 62.19, 52.01, 33.17, 29.42, 23.90
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