Diisopropylamine → Methyl 1,2,3,4-tetrahydro-6-methoxy-1-oxo-2-naphthaleneacetate

HRID 2119234Notes

Reaction equation

HRID 2119234 reaction equation
[Li+].CC([N-]C(C)C)C.C(NC(C)C)(C)C.C([Li])CCC.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[CH2:28][CH2:27][CH2:26]2.Br[CH2:35][C:36]([O:38][CH3:39])=[O:37]>C1COCC1>[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[CH:28]([CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH2:27][CH2:26]2

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 141126-Methoxy-alpha-tetraloneHCID 60984Methyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 13934507Methyl 1,2,3,4-tetrahydro-6-methoxy-1-oxo-2-naphthaleneacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LDA, prepared from diisopropylamine (0.84 ml) and n-butyl lithium (3.44 ml, 1.6 M in hexane) in 10 ml of THF at -78° was added dropwise a solution of 6-methoxy-1-tetralone (0.88 g, 5.0 mmol) in 5 ml of THF in an atmosphere of nitrogen. To the stirred solution at -78° was then added methyl bromoacetate (0.5 ml, 6.0 mmole) and the mixture was allowed to warm to room temperature. Aqueous work-up and extraction with ether gave, after chromatography on silica gel, the title compound, m.p. 110°-112°.

Workup

  1. customat -78°
  2. extractionAqueous work-up and extraction with ether
  3. customgave

Sources & evidence

ORD record
ord-5b14c40e89b04f838ce61bc5dcb293cf
Source dataset
uspto-grants-1987_07
Patent number
US04683325

Reaction notes

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