Dichloromethane → HCID 19936246, compound

HRID 36835Notes

Reaction equation

HRID 36835 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]([CH2:12]O)([CH2:10]O)[CH2:8]O)([CH3:4])([CH3:3])[CH3:2].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.ClCCl>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:14])[C:7]([CH2:12][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22])([CH2:10][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22])[CH2:8][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 73974-Toluenesulfonyl chlorideHCID 19936248HCID 19936248, compound

Product 1

HCID 19936246HCID 19936246, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of t-butyl-tris(hydroxymethyl)acetate (9.9 g, 0.048 mol) in 50 mL of pyridine is cooled to 0° C. and then portions of p-toluenesulfonyl chloride (30.1 g, 0.158 mol) are added over 1 hr. The mixture is kept at 0° C. for 15 hrs. Then dichloromethane (200 mL) is added and the solution is washed four times with 100 mL of 10% hydrochloric acid, once with 100 mL of saturated sodium bicarbonate and once with 100 mL of saturated sodium chloride. The organic layer is dried over anhydrous sodium sulfate and evaporated under reduced pressure to give t-butyl-tris(tosylmethyl)acetate.

Workup

  1. washthe solution is washed four times with 100 mL of 10% hydrochloric acid
  2. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b6fd7d535366451c8025d980379ea4c5
Source dataset
uspto-grants-1995_05
Patent number
US05417959

Reaction notes

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