Carbon Dioxide → 8-methoxy-3,4-dihydro-1H-naphthalene-2,2-dicarboxylic acid methyl ester

HRID 1243138Notes

Reaction equation

HRID 1243138 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([O:15][CH3:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[Li+].CC([N-]C(C)C)C.[C:25](=[O:27])=[O:26]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([C:25]([OH:27])=[O:26])[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([O:15][CH3:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 2724682Lithium diisopropylamideHCID 13058286Methyl 8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Product 1

HCID 695851948-methoxy-3,4-dihydro-1H-naphthalene-2,2-dicarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF (1.0 mL) solution of 8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester (660 mg, 3.0 mmol) was added to freshly made LDA (made by addition of 2.0 mL of 2.3 M BuLi to 1.5 mL THF solution of 0.7 mL iPr2NH) at −78° C. and the mixture was allowed to stir for 1.5 hour. A CO2 balloon was then applied. The reaction mixture was quenched with aqueous NH4Cl and the resulting mixture was extracted with ethyl acetate (3×15 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to provide the crude-8-methoxy-3,4-dihydro-1H-naphthalene-2,2-dicarboxylic acid methyl ester (470 mg).

Workup

  1. customThe reaction mixture was quenched with aqueous NH4Cl
  2. extractionthe resulting mixture was extracted with ethyl acetate (3×15 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ba5de61eb164ad0ad04fdd54c3eee1e
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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