Diisopropylamine → HCID 14857308, compound

HRID 1195808Notes

Reaction equation

HRID 1195808 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH2:13]([N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]1=[O:26])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:27][C:28]1([CH3:41])[CH:37]2[O:38][CH:36]2[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:39]#[N:40])[CH:34]=2)[O:29]1>CCCCCC.C1COCC1.N#N.CO>[CH3:27][C:28]1([CH3:41])[CH:37]([OH:38])[CH:36]([C:22]2[C:21](=[O:26])[N:20]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:25]=[CH:24][CH:23]=2)[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:39]#[N:40])[CH:34]=2)[O:29]1

Participants

9

Reactant 4

HCID 7912DiisopropylamineHCID 2440781-Benzyl-2(1H)-pyridoneHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochromanHCID 178418339Butyllithium2×

Product 1

HCID 14857308HCID 14857308, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 947NitrogenSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

6.7 ml of a 15% solution of butyllithium in hexane are added to a solution of 1.4 ml of diisopropylamine in 10 ml of THF while stirring and passing in N2 at 0°. A solution of 1.85 g of N-benzyl-2-pyridone in 10 ml of THF at 0° is then added dropwise. After stirring for 0.5 hours, a solution of 2 g of 2,2-dimethyl-3,4-epoxy-6-cyanochroman in 10 ml of THF is added dropwise at 0°, the mixture is boiled for 2 hours and excess butyllithium is decomposed by adding methanol dropwise. Customary working up gives 2,2-dimethyl-4-(1-benzyl-1,2-dihydro-2-oxo-3-pyridyl)-6-cyano-3-chromanol, m.p. 120°-122°.

Workup

  1. stirringAfter stirring for 0.5 hours

Sources & evidence

ORD record
ord-8543381c467940d5a20f550ff8a9ffa7
Source dataset
uspto-grants-1992_05
Patent number
US05112839

Reaction notes

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