Benzaldehyde → HCID 54696188, compound

HRID 357801Notes

Reaction equation

HRID 357801 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.C(=O)[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:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:7][C:1](=[O:6])[CH:2]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 54696188HCID 54696188, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

The title compound was prepared as described in General Method 1 using 13.67 g methyl acetoacetate, 8.5 g of NaH 60% dispersion in oil, 73.6 mL of 1.6M n-butyl lithium in hexane, 10 g of benzaldehyde, and 300 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred 15 minutes at -78° C. then allowed to warm to room temperature overnight. A solid was filtered off after concentration (m.p. 145°-146° C.). 1H NMR (CDCl3) δ 2.8-3.05 (m, 2 H), 3.5 (d, 1 H), 3.7 (d, 1 H), 5.7 (dd, 1 H), 7.3-7.5 (m, 5 H).

Workup

  1. temperatureto warm to room temperature overnight
  2. filtrationA solid was filtered off
  3. concentrationafter concentration (m.p. 145°-146° C.)

Sources & evidence

ORD record
ord-e641d436f65e4508bc4ed1a7e8d495be
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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