Hydrochloric Acid → HCID 22349525, compound

HRID 896073Notes

Reaction equation

HRID 896073 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:11])=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.[CH:20]([Si:23](OS(C(F)(F)F)(=O)=O)([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])([CH3:22])[CH3:21].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[O:11][Si:23]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:20]([CH3:22])[CH3:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 27548246-bromo-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 22349525HCID 22349525, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 6-Bromo-2,3-dihydro-1H-inden-1-ol (300 mg, 1.41 mmol) in CH2Cl2 (4 mL) was added 2,6-lutidine (151 μL, 1.41 mmol) followed by triisopropylsilyltriflate (378 μL, 1.41 mmol) at room temperature. The reaction was stirred for 30 min then added to 1N HCl and extracted. The organic layer was washed with saturated sodium bicarbonate then brine and dried over MgSO4. The solvent was removed in vacuo and the crude material purified by column chromatography.

Workup

  1. extractionextracted
  2. washThe organic layer was washed with saturated sodium bicarbonate
  3. dry with materialbrine and dried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe crude material purified by column chromatography

Sources & evidence

ORD record
ord-591e89d93cee4268ba645c7de5d02c94
Source dataset
uspto-grants-2005_07
Patent number
US06919335B2

Reaction notes

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