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Sodium hydride → ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-fluoro-2-butenoate

HRID 1596550
Notes
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Reaction equation

HRID 1596550 reaction equation
[H-].[Na+].[F:3][CH:4](P(OCC)(OCC)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:18][CH:19]([N:21]1[C:30]2[C:25](=[CH:26][C:27]([C:31](=O)[CH3:32])=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1)[CH3:20].[Cl-].[NH4+]>CN(C)C=O>[CH3:20][CH:19]([N:21]1[C:30]2[C:25](=[CH:26][C:27](/[C:31](/[CH3:32])=[C:4](/[F:3])\[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1)[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 107751501-[1-(1-Methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl)ethanone

Product 1

HCID 10852120ethyl (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-fluoro-2-butenoateYield 81.9%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

450 mg (60%, 12 mmol) of sodium hydride was suspended in 10 ml of N,N-dimethylformamide. 3.3. g (14 mmol) of ethyl 2-fluoro-diethylphosphonoacetate was dropped into the suspension under cooling with ice. The obtained mixture was stirred under cooling with ice for 30 minutes, followed by the addition of 2.0 g (9.2 mmol) of 1-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl)ethanone. The obtained mixture was stirred under cooling with ice for onie hour, followed by the addition of an aqueous solution of ammonium chloride. The obtained mixture was extracted with ethyl acetate, and the organic phase was washed with a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and concentrated in a vacuum. The residue was purified by silica gel column chromatography to give 2.3 g of the title compound as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice for 30 minutes
  3. stirringThe obtained mixture was stirred
  4. temperatureunder cooling with ice for onie hour
  5. extractionThe obtained mixture was extracted with ethyl acetate
  6. washthe organic phase was washed with a saturated aqueous solution of common salt
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in a vacuum
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-79a76c057554427db6f31c7905268ced
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06291508B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes