Pyridine → HCID 14821670, compound

HRID 2352664Notes

Reaction equation

HRID 2352664 reaction equation
[F:1]/[C:2](/[S:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:7])=[CH:3]\[CH2:4][OH:5].N1C=CC=CC=1.[CH:20](OC(=O)C)=[O:21]>O>[CH:20]([O:5][CH2:4]/[CH:3]=[C:2](\[F:1])/[S:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:7])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 75269Acetic-formic anhydrideHCID 14821669HCID 14821669, compound

Product 1

HCID 14821670HCID 14821670, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of (E)-3-fluoro-3-hexylsulfinyl-2-propenol (0.21 g, 1.0 mmol) and 2 ml of pyridine cooled to -30° is added through syringe acetic-formic anhydride (0.4 ml). The mixture is allowed to warm to 10° over a period of 1 hour. It is then diluted with water, extracted with hexane, washed with aqueous 2N H2S04, then water, then aqueous NaHCO3, finally brine and is dried. The product is purified by prep. TLC to give (E)-3-fluoro-3-hexylsulfinyl-2-propenyl formate (cpd. 3, Table A).

Workup

  1. temperaturecooled to -30°
  2. temperatureto warm to 10° over a period of 1 hour
  3. extractionextracted with hexane
  4. washwashed with aqueous 2N H2S04
  5. dry with materialwater, then aqueous NaHCO3, finally brine and is dried
  6. customThe product is purified by prep

Sources & evidence

ORD record
ord-f4aad9cd2cf441d7b0bb4cf680a8ca88
Source dataset
uspto-grants-1989_10
Patent number
US04877899

Reaction notes

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