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Diisopropylamine → HCID 70069641, compound

HRID 1067302
Notes
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Reaction equation

HRID 1067302 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])C)([CH3:3])C.C([Li])CCC.[CH3:13][O:14][CH2:15][O:16][C:17](=[O:37])[CH2:18]/[C:19](/[C:33]([O:35][CH3:36])=[O:34])=[C:20](/[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([Cl:32])[CH:23]=1)\[CH3:21].[Cl-].[NH4+].[O:40]1CC[CH2:42][CH2:41]1>CCCCCC>[CH3:13][O:14][CH2:15][O:16][C:17](=[O:37])[CH:18]([CH:41]([C:42]1[CH:3]=[CH:1][N:4]=[CH:5][CH:7]=1)[OH:40])/[C:19](/[C:33]([O:35][CH3:36])=[O:34])=[C:20](/[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([Cl:32])[CH:23]=1)\[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran3×HCID 25517Ammonium ChlorideHCID 70070414HCID 70070414, compoundHCID 178418339Butyllithium

Product 1

HCID 70069641HCID 70069641, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (1.33 ml) in tetrahydrofuran (20 ml) is added gradually and dropwise a 1.6 N solution of n-butyl lithium in hexane (5.91 ml) at 0° C., and the mixture is stirred at the same temperature for 30 minutes. The solution is cooled to −78° C., and thereto is added gradually and dropwise a solution of (Z)-4-(3-chloro-4,5-dimethoxyphenyl)-4-methyl-3-methoxycarbonyl-3-butenoic acid methoxymethyl ester (2.94 g) in tetrahydrofuran (20 ml), and the mixture is further stirred at the same temperature for 30 minutes. The reaction mixture is cooled to −90° C., and thereto is added gradually and dropwise a solution of isonictinaldehyde (1.01 g) in tetrahydrofuran (10 ml), and the mixture is stirred at −90° C. for 20 minutes. To the reaction mixture is added a saturated aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. The organic layer is washed, dried, and concentrated under reduced pressure to remove the solvent to give (Z)-4-(3-chloro-4,5-dimethoxyphenyl)-4-methyl-3-methoxycarbonyl-2-(4-pyridylhydroxymethyl)-3-butenoic acid methoxymethyl ester.

Workup

  1. additionis added gradually
  2. temperatureThe reaction mixture is cooled to −90° C.
  3. additionis added gradually
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe organic layer is washed
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent

Sources & evidence

ORD record
ord-f566a2f0cc034778b0c865b0eb86ee36
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06248743B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes