Hydrochloric Acid → 7,8-Difluoro-5-iodo-2-pentylchroman-6-ol

HRID 2244841Notes

Reaction equation

HRID 2244841 reaction equation
Cl.[F:2][C:3]1[C:12]([F:13])=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[O:10]2)=[C:5]([I:19])[C:4]=1[O:20]COC>C1COCC1.CC(OC)(C)C>[F:2][C:3]1[C:12]([F:13])=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[O:10]2)=[C:5]([I:19])[C:4]=1[OH:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 592152607,8-Difluoro-5-iodo-6-methoxymethoxy-2-pentylchroman

Product 1

HCID 592152577,8-Difluoro-5-iodo-2-pentylchroman-6-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

9.2 ml of conc. HCl are added to a solution of 21.4 g (50.2 mmol) of 7,8-difluoro-5-iodo-6-methoxymethoxy-2-pentylchroman in 90 ml of THF, and the mixture is stirred at room temperature for 17 h. The batch is diluted with MTBE, and the solution is washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The crude product is purified by column chromatography (SiO2, n-heptane:MTBE=1:1), giving 7,8-difluoro-5-iodo-2-pentylchroman-6-ol as a beige solid.

Workup

  1. washthe solution is washed with water
  2. extractionThe aqueous phase is extracted with MTBE
  3. washthe combined organic phases are washed with water and sat. sodium chloride soln
  4. customThe solution is dried
  5. concentrationconcentrated to dryness
  6. customThe crude product is purified by column chromatography (SiO2, n-heptane:MTBE=1:1)

Sources & evidence

ORD record
ord-8d6058bce2a94c9780855df87b4eda4d
Source dataset
uspto-grants-2010_03
Patent number
US07678929B2

Reaction notes

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