Water → Ethyl 2-(2-methoxyethyl)-pent-4-enoate

HRID 322617

反応式

HRID 322617 の反応式
[CH3:1][O:2][CH2:3][CH2:4][C:5]([CH2:16][CH:17]=[CH2:18])(C(OCC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[Cl-].[Li+].CN(C=O)C.O>CS(C)=O>[CH3:1][O:2][CH2:3][CH2:4][CH:5]([CH2:16][CH:17]=[CH2:18])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

参加物

6

反応物 4

HCID 962Water2 回HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 22011257Diethyl 2-(2-methoxyethyl)-2-allylmalonate

生成物 1

HCID 22011260Ethyl 2-(2-methoxyethyl)-pent-4-enoate収率 87.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A mixture of diester 2 (40 g, 155 mmol), prepared according to Example 1, and lithium chloride (13 g, 300 mmol) in DMSO (100 mL). DMF (20 mL), and water (2 mL) was heated to 170° C. for 6 h and cooled to room temperature. The mixture was poured into water (250 mL), extracted with CH2Cl2 (3×100 mL), and dried over MgSO4. The solvent was removed under reduced pressure to afford the monoester ether 3 (25.2 g, 87%); IR (KBr) υmax 3079, 2974, 2921, 2869, 1732, 1640, 1461, 1443, 1470, 1374, 1177, 1121, 1029, 990, 916, 855 cm−1; 1HNMR (CDCl3) δ1.25 (t, J=7.05 Hz, 3H), 1.65-1.75 (m, 1H), 1.85-1.95 (m, 1H), 2.20-2.40 (m, 2H), 2.50-2.60 (m, 1H), 3.30 (s, 3H), 3.35-3.45 (m, 2H), 4.13 (q, J=7.05, 2H), 5.00-5.07 (dd, J=10.2, 25 Hz, 2H), 5.71-5.74 (m, 1H); 13CNMR (CDCl3) δ14.21, 31.44, 36.45, 42.12, 58.48, 60.12, 70.37, 70.38, 116.79, 135.19, 175.19; mass spectrum (EI), m/Z (rel intensity) 223 (11), 200 (19), 185 (M-1, 4.5), 154 (19), 153 (46), 143 (33), 128 (33), 121 (37), 120 (34), 112 (22), 108 (88), 95 (28), 82 (41), 81 (98), 79 (94), 59 (38), 57 (71), 55 (100), 54 (38), 53 (59),

後処理

  1. customprepared
  2. extractionextracted with CH2Cl2 (3×100 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-a60a125a19cf4f8ba46d05f3420c1fd3
出典データセット
uspto-grants-2001_04
特許番号
US06211360B1

関連ノート

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