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

HRID 1111692Notes

Reaction equation

[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

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-349dd1bb5d6640228e2335ca792cfe29
Source dataset: uspto-grants-1978_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04118511

Reaction notes

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