Benzophenone → HCID 21222426, compound

HRID 357820Notes

Reaction equation

HRID 357820 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[H-].[Na+].C([Li])CCC.[C:16]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[C:17]1([C:16]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:23][C:1](=[O:6])[CH:2]=[CH:3][CH2:5]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 3102BenzophenoneHCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 21222426HCID 21222426, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared as described in General Method 1 using 20 mmol of methyl acetoacetate, 22 mmol of NaH 60% dispersion in oil, 21 mmol of 1.6M n-butyl lithium in hexane, 20 mmol of benzophenone and 70 mL of tetrahydrofuran. Upon concentrating the reaction a solid precipitated out which was triturated with ether and filtered (m.p. 170.5°-173° C.). 1H NMR (CDCl3) δ 3.18 (s, 2 H), 3.4 (s, 2 H), 7.3-7.5 (m, 10 H).

Workup

  1. concentrationUpon concentrating
  2. customthe reaction a solid
  3. customprecipitated out which
  4. customwas triturated with ether
  5. filtrationfiltered (m.p. 170.5°-173° C.)

Sources & evidence

ORD record
ord-f44388636e994308882c5f130ef1dfc2
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

Loading…