Isobutyraldehyde → HCID 89815985, compound

HRID 1521490Notes

Reaction equation

HRID 1521490 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2S(C2C=CC=CC=2)(=O)=O)=[CH:5][CH:4]=1.[Li]CCCC.[CH:26](=[O:30])[CH:27]([CH3:29])[CH3:28]>C1COCC1>[CH3:28][CH:27]([CH3:29])[C:26]([C:8]1[NH:9][C:10]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]([S:2][CH3:1])[CH:11]=2)=[O:30]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 89816088HCID 89816088, compoundHCID 178418339Butyllithium

Product 1

HCID 89815985HCID 89815985, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(methylthio)-1-(phenylsulfonyl)-1H-indole (890 mg, 2.93 mmol) in anhydrous THF (10 mL) at 0° C. under nitrogen was added n-BuLi (5.86 mL, 14.65 mmol, 2.5 M). After stirring for 30 min, isobutyraldehyde (1.05 g, 14.65 mmol) was added to the formed mixture. The reaction mixture was stirred at 0° C. for 1 h. The mixture was quenched with sat. NH4Cl (10 mL) at 0° C. and extracted with EtOAc (20 mL×3). The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated and purified by column chromatography on silica gel eluted with PE/EtOAc 20:1 to give 2-methyl-1-(6-(methylthio)-1H-indol-2-yl)propan-1-one (440 mg, 64.28% yield) as a colorless oil. LC-MS MS (ESI) m/z 234.1 [M+H]+. 1H NMR (CDCl3 400 MHz): δ 8.86 (brs, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.19 (s, 1H), 7.14-7.11 (m, 1H), 7.01 (dd, J1=8.4 Hz, J2=1.6, 1H), 3.42-3.38 (m, 1H), 2.47 (s, 3H), 1.20 (d, J=6.8 Hz, 6H).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 1 h
  2. customThe mixture was quenched with sat. NH4Cl (10 mL) at 0° C.
  3. extractionextracted with EtOAc (20 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography on silica gel
  8. washeluted with PE/EtOAc 20:1

Sources & evidence

ORD record
ord-c541e8336d5d4e4aa1a3b81b07521ccf
Source dataset
uspto-grants-2015_07
Patent number
US09073931B2

Reaction notes

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