Methyl iodide → 8-Methoxy-2-methyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester

HRID 1243130Notes

Reaction equation

HRID 1243130 reaction equation
N(C(C)C)[CH:2](C)C.[Li]CCCC.[CH3:13][O:14][C:15]([CH:17]1[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([O:27][CH3:28])[CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:16].CI.[NH4+].[Cl-]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH3:13][O:14][C:15]([C:17]1([CH3:2])[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([O:27][CH3:28])[CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:16]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 13058286Methyl 8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylateHCID 178418339Butyllithium

Product 1

HCID 695851218-Methoxy-2-methyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To iPr2NH (202 mg, 2.0 mmol) in THF (1.0 mL) was added BuLi (2.5 M, 0.8 mL, 2.0 mmol) at −78° C. After 10 minutes, 8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester in THF (1.0 mL) was added and the reaction mixture turned yellow. Methyl iodide (568 mg, 4.0 mmol) and HMPA (1.0 mL) were added after 30 minutes. The reaction mixture was allowed to stir at −78° C. for 3 hours at ambient temperature before aqueous NH4Cl was added. The mixture was extracted with ethyl acetate (3×20 mL) and the combined extracts were dried over MgSO4 and purified by column chromatography to give 8-methoxy-2-methyl-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester (170 mg, 84%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  3. dry with materialthe combined extracts were dried over MgSO4
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-8bbe002405d94a3e9158b9eabddb9607
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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