Water → HCID 14932533, compound

HRID 1792384Notes

Reaction equation

HRID 1792384 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.O>ClCCl.C(OCC)(=O)C.CCCCCC>[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1864034-(Dimethyl-tert-butylsilyl)oxybutan-1-ol

Product 1

HCID 14932533HCID 14932533, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(t-butyldimethylsilyloxy)-1-butanol (2.8 g, 13.7 mmol) in dichloromethane (30 ml) were added triethyamine (3.83 ml, 27.4 mmol) and p-toluenesulfonyl chloride (2.88 g, 15.1 mmol) at 0° C., which was then stirred at the same temperature for 2 hours. After the reaction was completed, water was added to the reaction mixture. The resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=5:1) to give the title compound (4.0 g, yield: 81%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product
  5. customThis crude product thus obtained

Sources & evidence

ORD record
ord-2235ddf34e06478eb42a7b73609e4d6d
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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