Methyl acetoacetate → HCID 54703382, compound

HRID 481864Notes

Reaction equation

HRID 481864 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[CH2:16]1[CH2:26][C:24](=O)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21]C=2)[CH2:17]1>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][C:8]2([C:23]3[C:18](=[CH:17][CH:16]=[CH:26][CH:24]=3)[CH2:19][CH2:20][CH2:21]2)[O:7][C:1](=[O:6])[CH:2]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 107241-TetraloneHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 54703382HCID 54703382, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared as described in General Method 1 using 25 mmol of methyl acetoacetate, 27.5 mmol of NaH 60% dispersion in oil, 26.25 mmol of 1.6M n-butyl lithium in hexane, 25 mmol of α-tetralone and 70 mL of tetrahydrofuran. The product was recrystallized from ethyl acetate/diethyl ether (m.p. 117°-119° C.). 1H NMR (CDCl3) δ1.7-1.9 (m, 1H), 1.9-2.1 (m, 2H), 2.1-2.3 (m, 1H), 2.7-3.0 (m, 2H), 2.95 (d, 1H), 3.1 (d, 1H), 3.5 (s, 2H), 7.1-7.2 (m, 1H), 7.2-7.3 (m, 2H), 7.4-7.5 (m, 1H).

Workup

  1. customThe product was recrystallized from ethyl acetate/diethyl ether (m.p. 117°-119° C.)

Sources & evidence

ORD record
ord-bfde928aa92041eaa2d57e654fbab0d5
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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