2-Chloromethyl 2-(trimethylsilyl)ethyl ether → HCID 86745670, compound

HRID 1030283Notes

Reaction equation

HRID 1030283 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([C:14]([O:16][CH3:17])=[O:15])=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].CC(C)([O-])C.[K+].[CH3:24][Si:25]([CH3:32])([CH3:31])[CH2:26][CH2:27][O:28][CH2:29]Cl>CN(C=O)C.C1COCC1>[CH3:24][Si:25]([CH3:32])([CH3:31])[CH2:26][CH2:27][O:28][CH2:29][N:9]1[C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([C:14]([O:16][CH3:17])=[O:15])[N:6]=[C:5]1[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 14955796Dimethyl 2-butyl-1H-imidazole-4,5-dicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86745670HCID 86745670, compoundYield 106%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

The diester 1 from Step (a) (23 g, MW 240, 0.096 mol) was dissolved in 300 ml DMF. Potassium t-butoxide (100 ml of a 1M solution in dry THF) was added through a syringe. The solution was stirred for 15 min at 25° C. [2-(trimethylsilyl)ethoxy]methyl chloride (SEM-chloride, 18.6 ml, 1.1 eq, MW 166, d 0.94) was added and a precipitate instantly formed. The reaction was stirred for 90 min at 25° C. The solvent was removed and the residue partitioned between ethyl acetate and water. The organic extract was dried over K2CO3 and concentrated. By TLC (SiO2, MeOH-CHCl3 /1-10) a single major spot was observed. This crude product (38 g, 106% yield) was used in subsequent steps without further purification.

Workup

  1. additionwas added
  2. customa precipitate instantly formed
  3. customThe solvent was removed
  4. customthe residue partitioned between ethyl acetate and water
  5. extractionThe organic extract
  6. dry with materialwas dried over K2CO3
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-083931cdec5a451692565c758970fdeb
Source dataset
uspto-grants-1992_04
Patent number
US05104891

Reaction notes

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