Tetrahydrofuran → HCID 66597331, compound

HRID 1627790Notes

Reaction equation

HRID 1627790 reaction equation
[CH2:1]([C:3]1[S:24][C:6]2=[N:7][C:8]([CH3:23])=[C:9]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)=[C:5]2[C:4]=1[CH3:25])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:36]1[CH2:40]OC[CH2:37]1.ICCC>CN(C=O)C>[CH2:1]([C:3]1[S:24][C:6]2=[N:7][C:8]([CH3:23])=[C:9]([CH:18]([CH2:37][CH2:36][CH3:40])[C:19]([O:21][CH3:22])=[O:20])[C:10]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)=[C:5]2[C:4]=1[CH3:25])[CH3:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 66597207HCID 66597207, compound

Product 1

HCID 66597331HCID 66597331, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure C from methyl 2-(2-ethyl-3,6-dimethyl-4-p-tolylthieno[2,3-b]pyridin-5-yl)acetate (0.196 g; 0.554 mmol), LHMDS 1N in THF (0.635 mL; 0.635 mmol), 1-iodopropane (0.090 mL; 0.923 mmol) in DMF (8 mL) for 3.5 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-15%) in heptane furnished 0.119 g (54%) of the title compound as a colorless oil.

Workup

  1. customThis compound was prepared
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (5-15%) in heptane

Sources & evidence

ORD record
ord-69e517432a7d4e859860bb3b90937282
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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