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

HRID 270150Notes

Reaction equation

HRID 270150 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 Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-4a51facb11084786b90bd8496d7c1722
Source dataset
uspto-grants-2008_11
Patent number
US07449468B2

Reaction notes

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