Tetrahydrofuran → HCID 49805489, compound

HRID 1627806Notes

Reaction equation

HRID 1627806 reaction equation
[CH3:1][C:2]1[C:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[C:13]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:12]2[C:11]3[CH2:10][CH2:9][O:8][CH2:7][C:6]=3[S:5][C:4]=2[N:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:37]1[CH2:41]OC[CH2:38]1.ICCC>CN(C=O)C>[CH3:1][C:2]1[C:14]([CH:15]([CH2:38][CH2:37][CH3:41])[C:16]([O:18][CH3:19])=[O:17])=[C:13]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[C:12]2[C:11]3[CH2:10][CH2:9][O:8][CH2:7][C:6]=3[S:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 336431-IodopropaneHCID 2733832Lithium HexamethyldisilazideHCID 66597223HCID 66597223, compound

Product 1

HCID 49805489HCID 49805489, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure C from methyl [2-methyl-4-(p-tolyl)-5,8-dihydro-6H-7-oxa-9-thia-1-aza-fluoren-3-yl]acetate (0.270 g; 0.73 mmol), LHMDS 1N in THF (0.8 mL; 0.8 mmol), 1-iodopropane (0.122 mL; 1.09 mmol) in DMF (3 mL) for 19 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane furnished 0.089 g (30%) of the title compound as a yellow oil.

Workup

  1. customThis compound was prepared
  2. customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (5-40%) in heptane

Sources & evidence

ORD record
ord-17653f88219448499fc0255fbd0abb54
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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