Ammonium Chloride → HCID 178450035, compound

HRID 480470Notes

Reaction equation

HRID 480470 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.Br[C:7]1[CH:20]=[CH:19][C:10]2[C:11]3[CH2:12][CH2:13][CH2:14][O:15][C:16]=3[CH:17]=[CH:18][C:9]=2[CH:8]=1.[CH:21]([C:23]1[N:24]=[CH:25][N:26](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:27]=1)=[O:22].[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH2:12]1[C:11]2[C:10]3[CH:19]=[CH:20][C:7]([C:21]([C:23]4[N:24]=[CH:25][NH:26][CH:27]=4)([OH:22])[CH:2]([CH3:3])[CH3:1])=[CH:8][C:9]=3[CH:18]=[CH:17][C:16]=2[O:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 18769153HCID 18769153, compoundHCID 178418339Butyllithium

Product 1

HCID 178450035HCID 178450035, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl-lithium in hexane (1.6M; 41 mL) was added to a solution of 8-bromo-2,3-dihydro-1H-benzo[f]chromene (13.35 g) in THF (250 ml) at −78° C. and stirred at the same temperature for 30 min. A solution of 4-formyl-1-trityl-1H-imidazole (16.83 g) in THF (150 ml) was added to the mixture and the whole was allowed to room temperature. Aqueous ammonium chloride solution was added to the mixture and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. The residue was washed with ethyl acetate to give the titled compound (11.80 g) as a colorless solid.

Workup

  1. customwas allowed to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-08c47f131e214a0c8fdeb6589b32ac47
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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