Water → 2-ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indole

HRID 1280821Notes

Reaction equation

HRID 1280821 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[O:12])[C:10]=2[CH:11]=1)[CH3:2].[H-].[Na+].C1(S(OC)=O)C=CC=CC=1.O>O1CCCC1.C(O)(=O)C>[CH2:1]([C:3]1[N:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[CH:7][CH:6]=2)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2759784Methyl benzenesulfinateHCID 184261202-ethyl-1,5,6,7-tetrahydro-1-(2-phenyl-phenylmethyl)-4H-indol-4-one

Product 1

HCID 106162052-ethyl-4-hydroxy-1-(2-phenyl-phenylmethyl)-1H-indoleYield 39.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-Ethyl-1,5,6,7-tetrahydro-1-(2-phenyl-phenylmethyl)-4H-indol-4-one (2.17 g, 0.0066 mol) dissolved in 10 mL of tetrahydrofuran was added to a slurry of sodium hydride (0.58 g) in 3 mL of tetrahydrofuran and the mixture was stirred for 15 min at room temperature. Methyl benzene sulfinate (1.13 g) was added and the solution stirred overnight. The reaction mixture was poured into water, the pH adjusted to 6 with acetic acid and extracted with toluene. The organic layer was separated, washed with water and brine, dried with sodium sulfate, concentrated, taken up in toluene (80 mL) and heated at reflux for 1.5 h. After cooling, the mixture was concentrated, dissolved in ether (100 mL), washed with saturated sodium bicarbonate solution, dried over sodium sulfate, concentrated and purified by flash chromatography on silica eluting with 10:1 hexane/ethyl acetate to afford 0.85 g of subtitled material.

Workup

  1. stirringthe solution stirred overnight
  2. extractionextracted with toluene
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. temperatureheated
  8. temperatureat reflux for 1.5 h
  9. temperatureAfter cooling
  10. concentrationthe mixture was concentrated
  11. dissolutiondissolved in ether (100 mL)
  12. washwashed with saturated sodium bicarbonate solution
  13. dry with materialdried over sodium sulfate
  14. concentrationconcentrated
  15. custompurified by flash chromatography on silica eluting with 10:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-af647e2880be4ad7aa6afee1ec02e6bc
Source dataset
uspto-grants-2002_09
Patent number
US06451839B1

Reaction notes

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