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

HRID 1111692노트

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HRID 1111692 반응식
[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

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydride2회HCID 21881883Oxolane--water (1/1)HCID 54274433HCID 54274433, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
40 °C

실험 절차

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 (m, 1H), 4.15 (m, 4H), 6.75-8.35 (7H), 8.15 (s, 1H).

후처리

  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)

출처 및 근거

ORD 기록
ord-349dd1bb5d6640228e2335ca792cfe29
출처 데이터셋
uspto-grants-1978_10
특허 번호
US04118511

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