Ethyl orthoformate → 4-t-Butyldimethylsilyloxymethyl-2-ethoxy-1,3-dithiolane

HRID 636871Notes

Reaction equation

HRID 636871 reaction equation
[Si:1]([O:8][CH2:9][CH:10]([SH:13])[CH2:11][SH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:14]([O:16][CH:17](OCC)OCC)[CH3:15].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][CH:10]1[CH2:11][S:12][CH:17]([O:16][CH2:14][CH3:15])[S:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 212558391-t-BUTYLDIMETHYLSILYLOXY-2,3-DIMERCAPTOPROPANE

Product 1

HCID 212558444-t-Butyldimethylsilyloxymethyl-2-ethoxy-1,3-dithiolaneYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-t-butyldimethylsilyloxy-2,3-dimercaptopropane (example 47) (32.00 g, 134 mmol) in toluene (400 mL) were added triethylorthoformate (29.0 mL, 174 mmol, 1.3 eq) and pyridinium p-toluenesulfonate (200 mg). The solution was stirred at 120°-130° C. for 6 hr then was quenched at room temperature with a solution of saturated sodium bicarbonate. The aqueous phase was extracted with dichloromethane and the organic layer was dried with magnesium sulfate and evaporated under reduced pressure. The crude product was obtained in 94% yield (37.17 g) as a 1:1 mixture and was used without further purification.

Workup

  1. customthen was quenched at room temperature with a solution of saturated sodium bicarbonate
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. dry with materialthe organic layer was dried with magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7d30f0ae188e42a781aeb4df529ed851
Source dataset
uspto-grants-2001_02
Patent number
US06194576B1

Reaction notes

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