Triphenylphosphine → 5-Fluoro-8-methoxychromane

HRID 1698690Notes

Reaction equation

HRID 1698690 reaction equation
[F:1][C:2]1[C:3]([CH2:11][CH2:12][CH2:13][OH:14])=[C:4](O)[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]2[C:3]=1[CH2:11][CH2:12][CH2:13][O:14]2

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 595119113-Fluoro-2-(3-hydroxypropyl)-6-methoxyphenol

Product 1

HCID 595118145-Fluoro-8-methoxychromaneYield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-74 °C

Procedure

After dissolving 4.78 g of 3-fluoro-2-(3-hydroxypropyl)-6-methoxyphenol and 9.4 g of triphenylphosphine in 70 ml of THF under a nitrogen atmosphere, the solution was cooled to −74° C. Next, 7 ml of DIAD was added to the reaction mixture, and the temperature was raised to room temperature prior to stirring overnight. The reaction mixture was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (3.6 g) as an oil.

Workup

  1. temperaturethe temperature was raised to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-a9a31b6bcfdf45bf911c0565aabf6192
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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