Hydrochloric Acid → HCID 59199340, compound

HRID 2089553Notes

Reaction equation

HRID 2089553 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[N:12]([CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[Cl:22])[C:15](=[O:23])[C:14]2([CH3:25])[CH3:24])[CH:11]=[N:10][CH:9]=1)(C)(C)C.Cl.O1CCOCC1>CO.C([O-])(O)=O.[Na+]>[Cl:22][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:21]=1[CH:13]([N:12]1[C:8]([CH2:7][OH:6])=[CH:9][N:10]=[CH:11]1)[C:14]([CH3:25])([CH3:24])[C:15]2=[O:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131730561HCID 131730561, compound

Product 1

HCID 59199340HCID 59199340, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[5-(tert-butyl-dimethyl-silanyloxymethyl)-imidazol-1-yl]-4-chloro-2,2-dimethyl-indan-1-one (2.4 g, 5.9 mmol) in methanol (40 mL) is added a 4N solution of HCl in 1,4-dioxane (9 mL, 36 mmol). The reaction is permitted to stir for 30 minutes, at which time the reaction is cooled to 0° C. and diluted with saturated aqueous NaHCO3. The reaction mixture is then concentrated in vacuo to ca. one fourth of the original volume and diluted with ethyl acetate. The layers are separated and the aqueous layer is extracted two times with ethyl acetate. The combined organic extracts are dried over Na2SO4, filtered and concentrated. The resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:19) to furnish 4-chloro-3-(5-hydroxymethyl-imidazol-1-yl)-2,2-dimethyl-indan-1-one; HRMS: (ESI) m/z 291.0909 [(M+H)+: Calcd for C15H16N2O2Cl: 291.0909]; 1H NMR (400 MHz, CD3OD) δ ppm 0.91 (s, 3 H), 1.40 (s, 3 H), 4.80 (d, J=4.29 Hz, 2 H), 5.88 (s, 1 H), 6.89 (s, 1 H), 6.97 (s, 1 H), 7.69 (t, J=7.71 Hz, 1 H), 7.79-7.87 (m, 2 H).

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo to ca. one fourth of the original volume
  2. additiondiluted with ethyl acetate
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted two times with ethyl acetate
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel flash chromatography (methanol-dichloromethane, 0:1 to 1:19)

Sources & evidence

ORD record
ord-d326c2ba0acf40dfa337d0556aa5a9e6
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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