Diethyl Ether → HCID 11750530, compound

HRID 1582651Notes

Reaction equation

HRID 1582651 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([C:15]3[CH:20]=CN=CC=3)[C:13](C)=[C:12]([C:22](OCC)=O)[C:11]=2[CH:27]([CH3:29])[CH3:28])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:38][CH2:39][CH3:40])C>>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH2:13][C:12]3[CH:22]=[CH:10][N:14]=[CH:13][CH:12]=3)[C:15]([CH3:20])=[C:40]([CH2:39][OH:38])[C:11]=2[CH:27]([CH3:28])[CH3:29])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 22718489HCID 22718489, compound

Product 1

HCID 11750530HCID 11750530, compound

Conditions

Temperature
2.5 °C

Procedure

A solution containing 0.1 g of ethyl 5-(3,5-dichlorophenylsulphanyl)-4-isopropyl-2-methyl-1-pyridin-4-yl-1H-pyrrole-3-carboxylate in 0.5 ml of anhydrous diethyl ether was added dropwise to 0.54 ml of a 1M solution of lithium aluminum hydride which was stirred and cooled at 0-5° C. The mixture was stirred at 5° C. for 1 h then at room temperature for 1 h. The mixture was cooled again to 5° C. and quenched with saturated ammonium chloride solution, then extracted three times with 10 ml of ethyl acetate. The combined extracts were washed with 10 ml of brine, then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using methanol/dichloromethane (1:19) for the elution to give 70 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole-3-methanol as a pale orange gum. Mass spectrum (ESI) m/z 421 [M+H]+. 1H NMR (CDCl3) 1.31 (d, 6H), 2.21 (s, 3H), 3.24 (m, 1H), 4.66 (s, 2H), 5.10 (s, 2H), 6.68 (d, 2H), 6.74 (m, 2H), 6.98 (t, 1H), 8.44 (m, 2H).

Workup

  1. stirringThe mixture was stirred at 5° C. for 1 h
  2. temperatureThe mixture was cooled again to 5° C.
  3. customquenched with saturated ammonium chloride solution
  4. extractionextracted three times with 10 ml of ethyl acetate
  5. washThe combined extracts were washed with 10 ml of brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography on silica gel
  10. washfor the elution

Sources & evidence

ORD record
ord-9abc63360b444f18b11293ab66af6d7c
Source dataset
uspto-grants-2004_05
Patent number
US06737429B2

Reaction notes

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