Ammonium Chloride → 5-Fluoro-1-(methoxymethylidene)-2,3-dihydro-1H-indene-4-carbonitrile

HRID 2173245Notes

Reaction equation

HRID 2173245 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[F:29][C:30]1[CH:38]=[CH:37][C:36]2[C:35](=O)[CH2:34][CH2:33][C:32]=2[C:31]=1[C:40]#[N:41].[NH4+].[Cl-]>C1COCC1>[F:29][C:30]1[CH:38]=[CH:37][C:36]2[C:35](=[CH:2][O:3][CH3:4])[CH2:34][CH2:33][C:32]=2[C:31]=1[C:40]#[N:41]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 552745775-fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrileHCID 178418339Butyllithium

Product 1

HCID 1317329685-Fluoro-1-(methoxymethylidene)-2,3-dihydro-1H-indene-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of (METHOXYMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE (1.3 g, 3.8 mmol) in THF (15 ml) was dropped n-Butyl Lithium (3.85 ml, 3.85 mmol) at −20° C. The mixture was stirred for 20 minutes before a THF solution of 5-Fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrile (450 mg, 2.6 mmol) was added into the reaction. TLC showed some green color spot right away. The reaction was then poured into NH4Cl, extracted with EtOAc, and flashed through silica gel. LC-MS (1E, m/z): 204 [M+1]+.

Workup

  1. additionwas added into the reaction
  2. extractionextracted with EtOAc

Sources & evidence

ORD record
ord-06ee60df70de452eaf2f11131a590465
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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