Triphenylphosphine → 5-Fluoro-8-methoxychromane

HRID 1161440Notes

Reaction equation

HRID 1161440 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 allowed to rise 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. customto rise 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-f597a51b1f4745179847006cdc257073
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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