Water → HCID 22715096, compound

HRID 352135Notes

Reaction equation

HRID 352135 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([OH:12])[CH2:8][CH2:9][CH2:10][OH:11].[C:13]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C.O>CN(C)C=O.CN(C1C=CC=CN=1)C>[CH3:14][C:13]([Si:17]([CH3:19])([CH3:18])[O:11][CH2:10][CH2:9][CH2:8][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[OH:12])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 22715085HCID 22715085, compound

Product 1

HCID 22715096HCID 22715096, compoundYield 51.8%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of the product from step (a) (0.67 g), tert-butylchlorodimethylsilane (0.6 g), triethylamine (0.56 ml) and dimethylaminopyridine (0.01 g) in dimethylformamide (5 ml) was stirred for 2hat 0° C. and at 20° C. for 16 h. Water was added and the mixture was extracted with ethyl acetate (three times). The combined organic extracts were washed with water, dried (sodium sulphate), evaporated and purified by chromatography on silica eluting with petrol-acetone to give the sub-title compound as a colourless oil (0.58 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (three times)
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried (sodium sulphate)
  4. customevaporated
  5. custompurified by chromatography on silica eluting with petrol-acetone

Sources & evidence

ORD record
ord-de60b2398b184ec1910eef726177e709
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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