Methyl iodide → N-[1-(Methoxymethyl)-3-(1-naphthyloxy)propyl]-N-methylformamide

HRID 66421ノート

反応式

HRID 66421 の反応式
[CH:1]([O:3][CH2:4][CH:5]([NH:19][CH:20]=[O:21])[CH2:6][CH2:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=O.[H-].[Na+].CI.[CH2:26]1COCC1.O>C1COCC1>[CH3:1][O:3][CH2:4][CH:5]([N:19]([CH3:26])[CH:20]=[O:21])[CH2:6][CH2:7][O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 24758Sodium hydride2 回HCID 21881883Oxolane--water (1/1)HCID 54274433HCID 54274433、化合物

生成物 1

HCID 22754995N-[1-(Methoxymethyl)-3-(1-naphthyloxy)propyl]-N-methylformamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
40 °C

実験手順

A solution of 2-(formylamino)-4-(1-naphthyloxy)-1-butanol formate, described in Example 3, in THF (30 ml) is added dropwise to a suspension of 51% sodium hydride (600 mg) in THF (30 ml). The mixture is heated at 40° C. for one and a half hours and then cooled to room temperature. A solution of methyl iodide (2.4 g) in THF (10 ml) is added and the mixture stirred at room temperature for 18 hours. Excess sodium hydride is decomposed by the addition of THF/water (9:1). The mixture is filtered through diatomaceous earth (Celite). The filtrate is dried and evaporated to dryness. The oily residue is subjected to chromatography on silica gel. Elution with methanol-chloroform (1:30) gives the title compound, nmr(CDCl3) δ 2.05 (m, 2H), 2.85 (s, 3H), 3.35 (s, 3H), 3.6 L (m, 1H), 4.15 (m, 4H), 6.75-8.35 (7H), 8.15 (s, 1H).

後処理

  1. temperaturecooled to room temperature
  2. filtrationThe mixture is filtered through diatomaceous earth (Celite)
  3. customThe filtrate is dried
  4. customevaporated to dryness
  5. washElution with methanol-chloroform (1:30)

出典と根拠

ORDレコード
ord-308592a7e8d149f18f268d50eb32c9e9
出典データセット
uspto-grants-1978_12
特許番号
US04131745

反応ノート

読み込み中…