Sodium Sulfate → 2-(5-bromo-1H-inden-2-yl)ethanol

HRID 551539Notes

Reaction equation

HRID 551539 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH2:6][C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([Br:14])=[CH:9][CH:8]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[Br:14][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH2:6][C:5]([CH2:4][CH2:3][OH:2])=[CH:13]2

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 85969236methyl(5-bromo-1H-inden-2-yl)acetate

Product 1

HCID 671042662-(5-bromo-1H-inden-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

The product from Example 52C (1.1 g, 4.1 mmol) in diethyl ether (5 mL) was added dropwise to a suspension of lithium aluminum hydride (0.125 g, 3.3 mmol) in diethyl ether (10 mL) maintaining the internal temperature below 10° C. After stirring for 30 minutes, the reaction mixture was diluted with diethyl ether (10 mL), cooled to 0° C., and treated with saturated aqueous sodium sulfate dropwise. The ethereal solution was decanted, dried with sodium sulfate, filtered, and the filtrate was concentrated to provide the title compound which was used without further purification in the next step. 1H NMR (CDCl3) δ 2.77 (m, 2H); 3.32 (s, 2H); 3.88 (t, J=6.5 Hz, 2H); 6.56 (m, 1H), 7.23 (m, 2H); 7.40 (m, 1H).

Workup

  1. temperaturemaintaining the internal temperature below 10° C
  2. customThe ethereal solution was decanted
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f61dfd52cc3e4d43aaf745a58b91d275
Source dataset
uspto-grants-2011_05
Patent number
US07947711B2

Reaction notes

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