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

HRID 322618ノート

反応式

HRID 322618 の反応式
[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]

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22011260Ethyl 2-(2-methoxyethyl)-pent-4-enoate

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-892e8b4410bf483f805c67d040d2a05d
出典データセット
uspto-grants-2001_04
特許番号
US06211360B1

反応ノート

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