Triphenylphosphine → 5-Fluoro-8-methoxychromane

HRID 1157930Notes

Reaction equation

HRID 1157930 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 mixture was cooled to −74° C. Next, 7 ml of DIAD was added to the reaction mixture, which was then raised to room temperature and stirred overnight. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate-heptane system) to obtain the target compound (3.6 g) as an oil.

Workup

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

Sources & evidence

ORD record
ord-9d62a0352ff64ff8b6e74796c9176ee0
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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