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

HRID 1280879ノート

反応式

HRID 1280879 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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, 2H), 2.88-2.91 (m, 2H), 3.01 (s, 3H), 3.87 (s, 3H), 4.40 (s, 2H), 7.40-7.53 (m, 6H), 7.60-7.62 (m, 4H), 7.90 (s, 2H).

後処理

  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

出典と根拠

ORDレコード
ord-5f1f068f027742619636f880944d8ea8
出典データセット
uspto-grants-2002_09
特許番号
US06451845B1

反応ノート

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