Thionyl Chloride → {[tert-Butyl(diphenyl)silyl]oxy}acetyl Chloride

HRID 1766118Notes

Reaction equation

HRID 1766118 reaction equation
[Si:1]([O:18][CH2:19][C:20]([OH:22])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:25])=O>C(Cl)Cl>[Si:1]([O:18][CH2:19][C:20]([Cl:25])=[O:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 111415642-((tert-Butyldiphenylsilyl)oxy)acetic acid

Product 1

HCID 19090360{[tert-Butyl(diphenyl)silyl]oxy}acetyl ChlorideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 500 ml round-bottom flask was mixed {[tert-butyl(diphenyl)silyl]oxy}acetic acid (17 g, 54.0 mmoles, 1 eq), thionyl chloride (11.7 g, 0.162 moles, 3 eq) and dry CH2Cl2 (120 ml, 0.45M). This mixture was refluxed for 5 hours. After cooling to room temperature the volatiles were removed in vacuo. The resulting residue was washed twice with toluene and the toluene was subsequently removed in vacuo to remove excess thionyl chloride. This resulted in 18 g (100%) of titled compound.

Workup

  1. temperatureThis mixture was refluxed for 5 hours
  2. customwere removed in vacuo
  3. washThe resulting residue was washed twice with toluene
  4. customthe toluene was subsequently removed in vacuo
  5. customto remove excess thionyl chloride

Sources & evidence

ORD record
ord-71cb4c5f379f421eb599e83bc79b10af
Source dataset
uspto-grants-2007_06
Patent number
US07229998B2

Reaction notes

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