Methyl acetoacetate → HCID 54696342, compound

HRID 357802Notes

Reaction equation

HRID 357802 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[C:16]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])[CH2:17][CH:18]([CH3:20])[CH3:19]>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][C:16]([CH2:17][CH:18]([CH3:20])[CH3:19])([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:21][C:1](=[O:6])[CH:2]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 68493IsovalerophenoneHCID 178418339Butyllithium

Product 1

HCID 54696342HCID 54696342, 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 12 g methyl acetoacetate, 4.3 g of NaH 60% dispersion in oil, 64.5 mL of 1.6M n-butyl lithium in hexane, 10 g of iso-valerophenone, and 300 mL of tetrahydrofuran. After addition of the phenone, the reaction was stirred 15 minutes at -78° C. and 2 hours at room temperature. The crude reaction was flash chromatographed using hexane/ethyl acetate 6/40-40/60 as eluent. The solid was triturated from diethyl ether (m.p. 123.5°-125° C.). 1H NMR (CDCl3) δ 0.81 (d, 3 H), 0.89 (d, 3 H), 1.6-1.7 (M, 1 H), 1.91 (m, 2 H), 2.90 (d, 1 H), 2.95 (d, 1 H), 3.25 (d, 1 H), 3.35 (d, 1 H), 7.25-7.45 (m, 5 H).

Workup

  1. customThe crude reaction
  2. customchromatographed
  3. customThe solid was triturated from diethyl ether (m.p. 123.5°-125° C.)

Sources & evidence

ORD record
ord-a3757d84a41349619ea2eb5534c4bb4f
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

Loading…