Sodium hydride → Methyl 1-(2-methoxy-ethoxymethyl)-naphthalene-2-carboxylate

HRID 1858807Notes

Reaction equation

HRID 1858807 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[H-].[Na+].[CH3:18][O:19][CH2:20][CH2:21][O:22][CH2:23]Cl>O1CCCC1>[CH3:18][O:19][CH2:20][CH2:21][O:22][CH2:23][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl esterHCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 22128610Methyl 1-(2-methoxy-ethoxymethyl)-naphthalene-2-carboxylateYield 38.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.3 g (11.4 mmol) of methyl 1-hydroxy-naphthalene-2-carboxylate in 15 ml of dry tetrahydrofuran was treated with 0.51 g (17 mmol) of sodium hydride (80%) and subsequently 2.13 g of 2-methoxyethoxymethyl chloride were added dropwise while cooling with ice. After 3 hours at room temperature the solution was extracted with aqueous sodium hydrogen carbonate solution and the organic phase was separated, dried over sodium sulphate and evaporated under reduced pressure. For purification, the crude product was chromatographed on silica gel using a 9:1 mixture of methylene chloride and ether as the eluent. In addition to 1.55 g of starting material there were obtained 1.2 g of methyl 1-(2-methoxy-ethoxymethyl)-naphthalene-2-carboxylate; MS: 290 (M)+.

Workup

  1. additionwere added dropwise
  2. temperaturewhile cooling with ice
  3. extractionAfter 3 hours at room temperature the solution was extracted with aqueous sodium hydrogen carbonate solution
  4. customthe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customFor purification
  8. customthe crude product was chromatographed on silica gel using
  9. additiona 9:1 mixture of methylene chloride and ether as the eluent
  10. additionIn addition to 1.55 g of starting material there

Sources & evidence

ORD record
ord-6f10929d1b5c4a90ae2e8d0e6781bdad
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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