Pyridine → HCID 68689066, compound

HRID 2238581Notes

Reaction equation

HRID 2238581 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6](O)[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:21])=O>C(OCC)C>[Cl:21][CH:6]1[C:5]2[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=2)[O:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 224047977-Fluorochroman-4-ol

Product 1

HCID 68689066HCID 68689066, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 7-fluorochroman-4-ol (1.80 g, 10.7 mmol, STEP 1) and pyridine (0.35 mL) in diethyl ether (14 mL) was added thionyl chloride (3.9 mL, 53.5 mmol) at 0° C. The reaction mixture was stirred at the same temperature for 3 hours, and evaporated to remove excess thionyl chloride. The residue was quenched with water, and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated in vacuum to afford the title compound as a pale brown solid (2.0 g, quant.):

Workup

  1. customevaporated
  2. customto remove excess thionyl chloride
  3. customThe residue was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-2de9b3cf82744e14b4af8377d049d22f
Source dataset
uspto-grants-2010_05
Patent number
US07718809B2

Reaction notes

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