Toluene → 2-Hydroxyethyl-1-(4-methylphenyl)sulfonyl-1H-indole

HRID 54846Notes

Reaction equation

HRID 54846 reaction equation
C(OC([C:6]1[N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])C2[C:13]([CH:14]=1)=CC=CC=2)=O)C.[OH-:25].[Na+].[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[OH:25][CH2:13][CH2:14][C:6]1[N:7]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:32]2[C:27]([CH:33]=1)=[CH:28][CH:29]=[CH:30][CH:31]=2

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 14783456Nod-IN-1

Product 1

HCID 162030902-Hydroxyethyl-1-(4-methylphenyl)sulfonyl-1H-indoleYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

To stirred solution of Red-A1 (sodium dihydro-bis(2-methoxyethoxy)aluminate≈70% in toluene) (30 mL) in dry THF (100 mL) cooled at 5° C. and under nitrogen was added dropwise and at this temperature a solution of compound of step 1 (26,8 g, 78 mmol) in dry THF (75 mL). After stirring one hour at 5° C. and then one hour at room temperature the mixture was cooled at 10° C. and treated dropwise with 2N NaOH, to effect hydrolysis of the intermediate complex. The organic phase was separated and the solvent in vacuo evaporated. The residue was solved in ethyl ether, the solution washed with water, dried over MgSO4 and evaporated to give the required alcohol (23.3 g, 98%) as a yellow oil; IR (film) 3500, 1597 cm-1.

Workup

  1. temperatureone hour at room temperature the mixture was cooled at 10° C.
  2. customhydrolysis of the intermediate complex
  3. customThe organic phase was separated
  4. customthe solvent in vacuo evaporated
  5. washthe solution washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-3ea63432e65e4a2ba31124427b761214
Source dataset
uspto-grants-1997_04
Patent number
US05622983

Reaction notes

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