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

HRID 322618노트

반응식

HRID 322618 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][CH2:10][CH:11]([CH2:17][CH:18]=[CH2:19])[C:12](OCC)=[O:13].O.[OH-].[Na+]>CCOCC>[CH3:7][O:8][CH2:9][CH2:10][CH:11]([CH2:17][CH:18]=[CH2:19])[CH2:12][OH:13]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22011260Ethyl 2-(2-methoxyethyl)-pent-4-enoate

생성물 1

HCID 220112592-(2-Methoxyethyl)-pent-4-en-1-ol수율 85.4%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-892e8b4410bf483f805c67d040d2a05d
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211360B1

반응 노트

불러오는 중…