Water → HCID 57519120, compound

HRID 1785361Notes

Reaction equation

HRID 1785361 reaction equation
[CH3:1][N:2]([CH3:19])[C:3](=[O:18])[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:15])[CH2:12][CH2:13][OH:14])=[C:7]([CH:16]=[CH2:17])[CH:6]=1.C(N([CH2:25][CH3:26])CC)C.[C:27]([Si:31]([CH3:34])([CH3:33])Cl)([CH3:30])([CH3:29])[CH3:28].O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:19][N:2]([CH3:1])[C:3](=[O:18])[O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:15])[CH2:12][CH2:13][O:14][Si:31]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:34]2[CH:26]=[CH:25][CH:12]=[CH:11][CH:8]=2)[C:33]2[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=2)=[C:7]([CH:16]=[CH2:17])[CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 17862026HCID 17862026, compound

Product 1

HCID 57519120HCID 57519120, compoundYield 139.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1,3-dihydroxy-propyl)-3-vinyl-phenyl dimethylcarbamate (4.44 g, 16.7 mmol) synthesized in step (e) of Example 192 in dichloromethane (40 ml) were added triethylamine (4.18 ml, 30.0 mmol), t-butyldimethylchlorosilane (4.67 g, 17.0 mmol) and a catalytic amount of 4-dimethylaminopyridine at −0° C. with stirring, and the resulting mixture was stirred for 5 hours at room temperature under a nitrogen atmosphere. After stirring, water (30 ml) was added to the reaction mixture, and the resulting mixture was extracted with dichloromethane (40 ml×2). The organic layer was washed successively with 1N hydrochloric acid (50 ml×1) and saturated aqueous sodium chloride solution (50 ml×1), dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo to afford the crude product. The crude product was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (2:1-1:1) as the eluent to afford the title compound (5.87 g, yield: 70%) as a colorless oil.

Workup

  1. stirringAfter stirring
  2. extractionthe resulting mixture was extracted with dichloromethane (40 ml×2)
  3. washThe organic layer was washed successively with 1N hydrochloric acid (50 ml×1) and saturated aqueous sodium chloride solution (50 ml×1)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford the crude product
  8. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-96b15e8c18704f68b411a33d85a9e40c
Source dataset
uspto-grants-2009_03
Patent number
US07504437B2

Reaction notes

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