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

HRID 1198614
Notes
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Reaction equation

HRID 1198614 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 6228DimethylformamideSolvent
HCID 8028
Tetrahydrofuran
Solvent

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-5083938f3f1b4b03aeaf00c4cf130df5
Source dataset
uspto-grants-1994_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05281615

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes