Sodium Chloride → HCID 68243108, compound

HRID 1844573Notes

Reaction equation

HRID 1844573 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Si:13]([O:30][CH2:31][CH2:32][C:33]([CH3:37])([CH3:36])[CH2:34]O)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:57]1(=[O:67])[NH:61][C:60](=[O:62])[C:59]2=[CH:63][CH:64]=[CH:65][CH:66]=[C:58]12.[Cl-].[Na+]>C1(C)C=CC=CC=1.O1CCCC1>[Si:13]([O:30][CH2:31][CH2:32][C:33]([CH3:36])([CH3:37])[CH2:34][N:61]1[C:57](=[O:67])[C:58]2[C:59](=[CH:63][CH:64]=[CH:65][CH:66]=2)[C:60]1=[O:62])([C:26]([CH3:27])([CH3:28])[CH3:29])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15946393HCID 15946393, compound

Product 1

HCID 68243108HCID 68243108, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of diethyl azodicarboxylate in toluene (2.2 M, 14.0 mL) was added to a solution of 4-{[tert-butyl(diphenyl)silyl]oxy}-2,2-dimethylbutan-1-ol (J. Am. Chem. Soc., 2007, vol. 129, p. 4456) (9.15 g), triphenylphosphine (7.40 g), and phthalimide (4.15 g) in tetrahydrofuran (150 mL) with stirring at room temperature. The mixture was stirred overnight at room temperature, and sodium chloride solution was then added thereto, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure, and diethyl ether was then added to the residue. Insoluble matter was filtered off through celite, and the filtrate was concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the title compound (11.8 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure, and diethyl ether
  5. additionwas then added to the residue
  6. filtrationInsoluble matter was filtered off through celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThen, the obtained crude product
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3012f9012a7149cbacbf4db4c6325e05
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

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