Water → Methyl 4-(4-formyl-2-methoxyphenoxy)butanoate

HRID 33986

반응식

HRID 33986 반응식
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[CH3:12][O:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:12][O:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17][O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7]

참가 물질

6

반응물 4

HCID 962WaterHCID 1183VanillinHCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrate

생성물 1

HCID 10753291Methyl 4-(4-formyl-2-methoxyphenoxy)butanoate수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of vanillin (47)(40.00 g, 262.89 mmol) and methyl-4-bromobutyrate (50.00 g, 276.18 mmol) in DMF (200 mL) was allowed to stir over potassium carbonate (51.53 g, 372.40 mmol) for 16 hours. Water was added to the reaction mixture at which time the product crystallised. The resulting mixture was filtered and dried in vacuo for 16 hours to afford the keto-ester (48) as a white solid (41.3 g, 66%). MP=57-59° C. 1H NMR (250 MHz, CDCl3) δ 9.80 (s, 1H), 7.46-7.40 (m, 2H), 6.97 (d, J=8.1 Hz, 1H), 4.16 (t, J=6.3 Hz, 2H), 3.92 (s, 3H), 3.70 (s, 3H), 2.57 (t, J=7.2 Hz, 2H), 2.20 (pent, J=6.7 Hz, 2H). 13C NMR (67.8 MHz, CDCl3) 188.2 (Cl), 173.7 (C12), 153.8 (Cquat.), 152.0 (Cquat.), 144.1 (Cquat.), 125.8 (Cmethine), 110.3 (C3), 108.5 (C6), 69.0 (C9), 57.0 (C8), 52.2 (C13), 30.6 (C11), 24.5 (C10). It was decided to adopt the numbering system shown in the figure below for the molecule for ease of peak assignment in 13C NMR.

후처리

  1. customcrystallised
  2. filtrationThe resulting mixture was filtered
  3. customdried in vacuo for 16 hours

출처 및 근거

ORD 기록
ord-44a5e748fd264f4bbf8f4ac6744d97fd
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429658B2

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