Methyl acetoacetate → HCID 54690720, compound

HRID 357823Notes

Reaction equation

HRID 357823 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[O:16]([CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][C:24]([CH2:23][O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[O:25][C:1](=[O:6])[CH:2]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 2221712-Phenoxy-1-phenylethan-1-oneHCID 178418339Butyllithium

Product 1

HCID 54690720HCID 54690720, 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 0.85 mL of methyl acetoacetate, 350 mg of NaH 60% dispersion in oil, 5 mL of 1.6M n-butyl lithium in hexane, 2.0 g of 2-phenoxy-1-phenyl ethanone and 60 mL of tetrahydrofuran. After addition of the ketone, the reaction was stirred for 15 minutes at 0° C. then allowed to warm to room temperature and stirred for 1 hour. The crude product was triturated from diethyl ether to afford a solid (m.p. 133°-135° C.). 1 H NMR (DMSO-d6) δ 3.03 (d, 1 H), 3.35 (d, 1 H), 4.18 (dd, 2 H), 4.90 (s, 1 H), 6.92-6.95 (m, 3 H), 7.24-7.49 (m, 7 H), 11.56 (s, 1 H).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 1 hour
  3. customThe crude product was triturated from diethyl ether

Sources & evidence

ORD record
ord-48f12f1cf79149418cfc90f929559c98
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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