Methyl acetoacetate → HCID 54721566, compound

HRID 357810Notes

Reaction equation

HRID 357810 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[C:16]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:19]([O:22][CH2:23]C=O)=[CH:18][CH:17]=1>CCCCCC.O1CCCC1>[C:16]1([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH:8]2[O:7][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 11413199HCID 11413199, compoundHCID 178418339Butyllithium

Product 1

HCID 54721566HCID 54721566, 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 4.76 g of methyl acetoacetate, 1.97 g of NaH 50% dispersion in oil, 19.5 mL of 2.1M n-butyl lithium in hexane, 8.7 g of [[1,1'-biphenyl]-4-yloxy]-acetaldehyde and 200 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 60 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. 152°-154° C.). 1H NMR (CDCl3) δ 2.83 (dd, 1 H), 2.95 (dd, 1 H) 3.61 (dd, 2 H), 4.23 (dd, 1 H), 4.38 (dd, 1 H), 5.03-5.07 (m, 1 H), 6.94-6.98 (m, 2 H), 7.30-7.57 (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-b83641a529fb41359895d1db1ea16158
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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