Methyl iodide → 2'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid methyl ester

HRID 1871290노트

반응식

HRID 1871290 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:11]([C:20]([OH:22])=[O:21])=[CH:10][C:9]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N12CCCN=C1CCCC[CH2:30]2.IC>C1COCC1>[CH3:30][O:21][C:20]([C:11]1[CH:10]=[C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1)=[O:22]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 234456652'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid

생성물 1

HCID 541817672'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid methyl ester수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

At 0° C., to a stirred solution of 2'-(2-methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid (1.72 g, 4.55 mmol) in THF (4.55 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene. After 0.5 h, to the reaction was added iodomethane and the reaction was stirred for 16 h, eventually warming to ambient temperature. The reaction was filtered and the filtrate concentrated. The crude product was dissolved in EtOAc, washed sequentially with sat. aq. NaHCO3 (3×), with 1 N HCl (3×), brine (3×), dried (K2CO3) and concentrated. Purification on Biotage KP-Sil eluting with 20% acetone/hexane gave 1.641 g (92%) of the title compound as a yellow oil. 1H NMR (DMSO-d6) δ 2.77-2.80 (m, 2 H), 2.88-2.91 (m, 2 H), 3.01 (s, 3 H), 3.87 (s, 3 H), 4.40 (s, 2 H), 7.40-7.53 (m, 6 H), 7.60-7.62 (m, 4 H), 7.90 (s, 2 H).

후처리

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated
  3. dissolutionThe crude product was dissolved in EtOAc
  4. washwashed sequentially with sat. aq. NaHCO3 (3×), with 1 N HCl (3×), brine (3×)
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated
  7. customPurification on Biotage KP-Sil
  8. washeluting with 20% acetone/hexane

출처 및 근거

ORD 기록
ord-d6fb872090e848ddab656c03adad35a7
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06103708

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