Sodium hydride → HCID 67003370, compound

HRID 2362629Notes

Reaction equation

HRID 2362629 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:16])[O:9][CH2:8][C:7]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)([OH:10])[CH2:6][O:5]1.Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:10][C:7]2([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)[CH2:8][O:9][C:4]([CH3:16])([CH3:3])[O:5][CH2:6]2)=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 58513749HCID 58513749, compound

Product 1

HCID 67003370HCID 67003370, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To an ambient suspension of sodium hydride (1.136 g, 47.3 mmol) in N,N-dimethylformamide (126 ml) was added 2,2-dimethyl-5-(thiazol-2-yl)-1,3-dioxan-5-ol (Example 11A) (8.15 g, 37.9 mmol) as a solution in N,N-dimethylformamide (20 mL). The reaction was stirred for 30 minutes, and tetrabutylammonium iodide (0.699 g, 1.893 mmol) and 1-(chloromethyl)-4-methoxybenzene (6.42 ml, 47.3 mmol) were sequentially added. The reaction was stirred overnight and then quenched by the addition of saturated aqueous ammonium chloride solution and ethyl acetate. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 0 to 40% ethyl acetate in hexane, to give the title product. MS ESI(+) m/z 336.0 [M+H]+.

Workup

  1. stirringThe reaction was stirred overnight
  2. customquenched by the addition of saturated aqueous ammonium chloride solution and ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate (2×)
  5. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with a gradient of 0 to 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-04a61e71c37940f6b5c3720a76ea9756
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

Loading…