Hydrochloric Acid → HCID 10446783, compound

HRID 2055726Notes

Reaction equation

HRID 2055726 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8]([C:15]([CH3:21])([CH3:20])[C:16]([O:18]C)=[O:17])[CH:7]=[CH:6][C:5]2=1.C[Si](C)(C)[O-].[K+].Cl>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8]([C:15]([CH3:21])([CH3:20])[C:16]([OH:18])=[O:17])[CH:7]=[CH:6][C:5]2=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668039Potassium trimethylsilanolateHCID 58616024HCID 58616024, compound

Product 1

HCID 10446783HCID 10446783, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-(6-Chloro-9H-carbazol-2-yl)-2-methyl-propionate in THF (1.5 mL) was added potassium trimethylsilanolate (189 mg, 2.5 eq) and the mixture heated to 50° C. for 3 hrs. The solution was diluted with EtOAc and acidified to ˜pH 3 with 2M HCl. The organic layer was separated and the aqueous phase extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and evaporated to dryness to afford the desired acid, 2-(6-chloro-9H-carbazol-2-yl)-2-methyl-propionic acid, as a colorless solid. 1H NMR (500 MHz, MeOD) δ 7.98 (1H, d, J=1.8 Hz), 7.96 (1H, d, J=8.1 Hz), 7.47 (1H, d, J=1.5 Hz), 7.37 (1H, d, J=8.6 Hz), 7.29 (1H, dd, J=8.6, 2.1 Hz), 7.21 (1H, d, J=8.4, 1.7 Hz), 1.63 (6H, s).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase extracted with EtOAc
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-1c4efc2313274be78b85021acd6466ba
Source dataset
uspto-grants-2008_02
Patent number
US07332516B2

Reaction notes

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