Methyl acetoacetate → HCID 54721634, compound

HRID 357837Notes

Reaction equation

HRID 357837 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[CH2:16]([N:23]([CH3:37])[C:24](=[O:36])[CH2:25][CH2:26][CH2:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[CH2:16]([N:23]([CH3:37])[C:24](=[O:36])[CH2:25][CH2:26][CH2:27][C:28]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:5][C:3]([OH:4])=[CH:2][C:1](=[O:6])[O:35]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 69838142HCID 69838142, compoundHCID 178418339Butyllithium

Product 1

HCID 54721634HCID 54721634, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared as described in General Method 1 using 5.6 mmol of methyl acetoacetate, 6.1 mmol of NaH 60% dispersion in oil, 5.9 mmol of 1.6M n-butyl lithium in hexane, 5.6 mmol of 5-oxo-5-phenylpentanoic acid benzyl-methyl amide and 25 mL of tetrahydrofuran. The product was flash chromatographed using CH2 Cl2 /MeOH (98/2) to give a solid (m.p. 47°-51° C.). 1H NMR (DMSO-d6) δ 1.1-1.3 (m, 1 H), 1.4-1.6 (m, 1 H), 1.8-2.0 (m, 2 H), 2.2-2.4 (m, 2 H), 2.75/2.81 (s/s 3 H), 2.85-3.1 (m, 2 H), 4.4/4.5 (s/s, 2 H), 4.85/4.9 (s/s 1 H), 7.1-7.4 (m, 10 H), 11.36/11.38 (s/s, 1 H).

Workup

  1. customchromatographed

Sources & evidence

ORD record
ord-3be7e07c5be840f896d2a283dd45cfb5
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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