Methyl acetoacetate → HCID 54721661, compound

HRID 357808Notes

Reaction equation

HRID 357808 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]([O:23][C:24]1[CH:31]=[CH:30][C:27](C=O)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][CH:8]([C:27]2[CH:30]=[CH:31][C:24]([O:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:25][CH:26]=2)[O:7][C:1](=[O:6])[CH:2]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 178418339Butyllithium

Product 1

HCID 54721661HCID 54721661, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared as described in General Method 1 using 5.0 mL of methyl acetoacetate, 2.0 g of NaH 60% dispersion in oil, 25 mL of 2.0M n-butyl lithium in hexane, 12.0 g of 4-benzyloxybenzaldehyde and 150 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 15 minutes at 0° C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 165°-166° C). 1H NMR (CDCl3) δ 2.91 (dd, 2 H), 3.56 (dd, 2 H), 5.09 (s, 2 H), 5.65 (dd, 1 H), 6.98-7.04 (m, 2 H), 7.30-7.44 (m, 7 H).

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe crude product was triturated from diethyl ether

Sources & evidence

ORD record
ord-82c9cd80e8f64a87b144d6e72d0bbd2f
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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