Methyl iodide → trans-N-(1,2,3,4-tetrahydro-4-methoxy-1-naphthyl)acetamide

HRID 372283Notes

Reaction equation

HRID 372283 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([NH:12][C:13](=[O:15])[CH3:14])[CH2:4][CH2:3]1.[CH3:16]I>[Ag]=O.O1CCCC1>[CH3:16][O:1][C@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]([NH:12][C:13](=[O:15])[CH3:14])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 6328Methyl iodide2×HCID 13037024N-(4-Oxo-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Product 1

HCID 70617063trans-N-(1,2,3,4-tetrahydro-4-methoxy-1-naphthyl)acetamide

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of racemic N-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)acetamide (3.9 g) and 150 ml. tetrahydrofuran (THF) is stirred and 17 ml. of methyl iodide and 24.4 g. of freshly prepared silver oxide are added over a 4-hour period, under a nitrogen atmosphere. After 16 hours, an additional 10 ml. of methyl iodide and 11.4 g. of silver oxide are added over a 4-hour period and stirring is continued for 2 days. The mixture is filtered through a layer of celite and the filter cake washed with THF (2 × 75 ml.). The filtrate and wash solution are combined and evaporated to dryness in vacuo to afford 4.3 g. of solid. The solid is recrystallized from hexane/ether to afford 2.4 g. of title compound, melting point 97°-100° C.

Workup

  1. waitis continued for 2 days
  2. filtrationThe mixture is filtered through a layer of celite and the filter cake
  3. washwashed with THF (2 × 75 ml.)
  4. washThe filtrate and wash solution
  5. customevaporated to dryness in vacuo
  6. customto afford 4.3 g
  7. customThe solid is recrystallized from hexane/ether
  8. customto afford 2.4 g

Sources & evidence

ORD record
ord-ee56eb2cb536446aa3b424cafc4775cb
Source dataset
uspto-grants-1978_05
Patent number
US04089976

Reaction notes

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