Potassium Carbonate → HCID 19595645, compound

HRID 612732Notes

Reaction equation

HRID 612732 reaction equation
C([O:4][C:5]1[C:6]2[CH2:7][CH2:8][C:9]([CH3:19])([CH3:18])[C:10]=2[CH:11]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:13]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[C:14]([C:12]1[CH:13]=[C:5]([OH:4])[C:6]2[CH2:7][CH2:8][C:9]([CH3:19])([CH3:18])[C:10]=2[CH:11]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 54402935HCID 54402935, compound

Product 1

HCID 19595645HCID 19595645, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the above indane 14 (0.36 g, 1.37 mmol) dissolved in 15 rnd. MeOH was added solid K2CO3 (0.38 g, 2.74 mmol). The reaction mixture was allowed to stir overnight at room temperature. MeOH was evaporated and the residue was diluted with 10 mL of water. The aqueous layer was then acidified with 5% HCl until pH=4 or 5. Aqueous layer was extracted with EtOAc (2×10 mL). Then the organic layer was washed with saturated NaCl and dried with Na2SO4. Organics were concentrated in vacuo to provide 0.25 g of the 6-t-butyl-1,1-dimethyl-indan-4-ol intermediate in 84% yield that was used directly into the next step. A solution of the above indane (0.25 g, 1.15 mmol) dissolved in 2 mL of dry pyridine was cooled to 0° C. Trifluoroacetic anhydride (0.36 mL, 2.13 mmol) was slowly added. Resulting mixture was allowed to warm to room temperature and was allowed to stir overnight. Reaction mixture was poured into 15 mL of water and extracted with ether (2×10 mL). Ether extract was sequentially washed with water (10 mL), 10% aq. HCl (2×10 mL), water (10 mL), and saturated NaCl. Organics were then dried with Na2SO4 and concentrated in vacuo to give 6-t-butyl-1,1-dimethyl-indan-4-ol triflate (15) as a clear oil in 77% yield. 1H NMR (400 MHz, CDCl3) δ7.13 (d, J=1.4 Hz, 1H, aromatic), 7.01 (d, J=1.2 Hz, 1H, aromatic), 2.95 (t, J=7.2 Hz, 2H, aliphatic CH2), 1.97 (t, J=7.2 Hz, 2H, aliphatic CH2), 1.31 (s, 9H, aliphatic 3CH3) 1.27 (s, 6H, aliphatic 2CH3).

Workup

  1. customMeOH was evaporated
  2. additionthe residue was diluted with 10 mL of water
  3. extractionAqueous layer was extracted with EtOAc (2×10 mL)
  4. washThen the organic layer was washed with saturated NaCl
  5. dry with materialdried with Na2SO4
  6. concentrationOrganics were concentrated in vacuo

Sources & evidence

ORD record
ord-7da7b6d6594b4a88a94ebeac7415f52e
Source dataset
uspto-grants-1999_12
Patent number
US06005007

Reaction notes

Loading…