Methyl acetoacetate → HCID 54721577, compound

HRID 357805Notes

Reaction equation

HRID 357805 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[CH3:16][C:17]([C:20]1[CH:27]=[CH:26][C:23](C=O)=[CH:22][CH:21]=1)([CH3:19])[CH3:18]>CCCCCC.O1CCCC1>[CH3:16][C:17]([C:20]1[CH:27]=[CH:26][C:23]([CH:8]2[O:7][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)=[CH:22][CH:21]=1)([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 703244-tert-ButylbenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 54721577HCID 54721577, 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, 31.5 mL of 1.6M n-butyl lithium in hexane, 9.0 g of 4-(1,1-dimethylethyl)benzaldehyde and 100 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. 164°-165° C.). 1 H NMR (CDCl3) δ 1.33 (s, 9 H), 2.94 (dd, 2 H), 3.59 (dd, 2 H), 5.69 (dd, 1 H), 7.31-7.47 (m, 4 H).

Workup

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

Sources & evidence

ORD record
ord-b8b85c1e63154dd89e1b05ff0e4d48c3
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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