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

HRID 322617노트

반응식

HRID 322617 반응식
[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]

참가 물질

6

반응물 4

HCID 962Water2회HCID 6228DimethylformamideHCID 433294Lithium ChlorideHCID 22011257Diethyl 2-(2-methoxyethyl)-2-allylmalonate

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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),

후처리

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

출처 및 근거

ORD 기록
ord-a60a125a19cf4f8ba46d05f3420c1fd3
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211360B1

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