Water → 2-(2-Methoxyethyl)-pent-4-en-1-ol

A 1M solution of lithium aluminum hydride (135 mL), 134 mmol) was added via cannula to a stirred solution of the ester 3 (25 g, 134 mmol), prepared according to Example 2, in dry ether (200 mL). The mixture was stirred for 2 h at room temperature under nitrogen and cooled to 0° C., and water (10 mL) was added dropwise, with stirring, followed by dropwise addition of 15% NaOH (10 mL) and water (30 mL) at 0° C. to produce a white precipitate. The precipitate was filtered, and washed with ether (2×50 mL). The filtrate was dried over MgSO4, filtered, and concentrated to give the alcohol 4 (16.5 g, 85.4%). IR (KBr) υmax 34,10, 3071, 2930, 2860, 1641, 1442, 1384, 1185, 1109, 1043, 993, 911 cm−1; 1HNMR (CDCl3) δ1.61-1.75 (m, 3 H), 2.02-2.30 (m, 2 H), 3.35 (s, 3 H), 3.36-3.60 (m, 4 H), 5.01-5.06 (m, 2 H), 5.77-5.79 (m, 1 H); 13CNMR (CDCl3): δ31.33, 35.95, 38.56, 58.20, 65.17, 70.98, 116.07, 136.59; mass spectrum (EI), m/z (rel intensity) 145 (7), 144 (M+, 3), 143 (23), 126 (15), 113 (20), 111 (42), 102 (17), 95 (27), 94 (57), 93 (31), 83 (49), 82 (41), 81 (61), 79 (100), 71 (70), 70 (42), 69 (38), 67 (65), 58 (46), 57 (34), 55 (75), 54 (48), 53 (34).

1. customprepared
2. temperaturecooled to 0° C.
3. stirringwith stirring
4. customto produce a white precipitate
5. filtrationThe precipitate was filtered
6. washwashed with ether (2×50 mL)
7. dry with materialThe filtrate was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-892e8b4410bf483f805c67d040d2a05d

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06211360B1