Diazomethane → Methyl 2,6-dihydroxy-4-pentylbenzoate

HRID 488671ノート

反応式

HRID 488671 の反応式
[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[C:7]([OH:16])[C:3]=1[C:4]([OH:6])=[O:5].[N+](=[CH2:19])=[N-]>CCOCC>[OH:1][C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:8]=[C:7]([OH:16])[C:3]=1[C:4]([O:6][CH3:19])=[O:5]

参加物

4

反応物 2

HCID 9550DiazomethaneHCID 3046173Benzoic acid, 2,6-dihydroxy-4-pentyl-

生成物 1

HCID 22271912Methyl 2,6-dihydroxy-4-pentylbenzoate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 2,6-dihydroxy-4-pentylbenzoic acid (2.0 g, 8.9 mM) in ether was treated with a 0.3 M solution of diazomethane in ether (30 mL) and stirred for 10 minutes. Nitrogen was bubbled through the solution for 10 minutes and then glacial acetic acid (4 drops). The reaction was concentrated under reduced pressure and purified by chromatography (5% ethyl acetate in hexanes) to give the desired product. MS ESI(−)) m/e 237 (M−H)+; 1H NMR (300 MHz, CDCl3) δ 9.62 (bs, 2H), 6.33 (s, 2H), 4.06 (s, 3H), 2.50 (t, 2H), 1.64-1.55 (m, 2H), 1.34-1.27 (m, 4H), 0.92-0.87 (m, 3H).

後処理

  1. customNitrogen was bubbled through the solution for 10 minutes
  2. concentrationThe reaction was concentrated under reduced pressure
  3. custompurified by chromatography (5% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-5fb5e418febd41c7b9ce1a8113a7047f
出典データセット
uspto-grants-2005_12
特許番号
US06972340B2

反応ノート

読み込み中…