Water → HCID 15117219, compound

HRID 1029615Notes

Reaction equation

HRID 1029615 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH2:10][C:9](O)([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8]1)=[O:6])[CH:2]=[CH2:3].S(Cl)(Cl)=O.O>N1C=CC=CC=1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][CH:10]=[C:9]([C:12]#[C:13][Si:14]([CH3:17])([CH3:15])[CH3:16])[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 15117218HCID 15117218, compound

Product 1

HCID 15117219HCID 15117219, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 1-allyloxycarbonyl-3-hydroxy-3-trimethylsilylethynylpyrrolidine (18.0 g) in pyridine (180 ml) was added dropwise thionyl chloride (29 ml) below 20° C. The resultant mixture was stirred for 1 hour and slowly poured into cooled water. The solution was extracted three times with n-hexane The extracts were combined, washed with 1N hydrochloric acid (4 times), saturated aqueous sodium hydrogen carbonate, water and brine successively, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel to give 1-allyloxycarbonyl-3-trimethylsilylethynyl-3-pyrroline (7.25 g).

Workup

  1. additionslowly poured
  2. extractionThe solution was extracted three times with n-hexane The extracts
  3. washwashed with 1N hydrochloric acid (4 times), saturated aqueous sodium hydrogen carbonate, water and brine successively
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-7480afdcb7bb446bb3ff28d1c458cea8
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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