Triphenylphosphine → HCID 18446948, compound

HRID 1268929Notes

Reaction equation

HRID 1268929 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH3:11][C@@H:12](O)[CH2:13][CH3:14].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:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C@H:12]([CH2:13][CH3:14])[CH3:11])[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 84682(-)-2-ButanolHCID 5872503-Fluoro-4-hydroxybenzaldehydeHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 18446948HCID 18446948, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 750 mg (5.4 mmol) of 3-fluoro-4-hydroxybenzaldehyde, 403 mg (5.4 mmol) of (R)-(−)-2-butanol and 2 g (7.5 mmol) triphenylphosphine in 10 mL of THF was treated with 1.5 mL of diisopropylazodicarboxylate. The resulting solution was stirred at rt for 14 h, cooled to rt and concentrated. Chromatography on a Biotage 40M cartridge using 4:1 v/v hexanes/Et2O as the eluant afforded 130 mg of the title compound: 1H NMR (500 Mhz) δ 0.99 (t, J=7.6, 3H), 1.35 (d, J=6.2, 3H), 1.58–1.83 (m, 2H), 4.47 (m, 1H), 7.05 (t, J=8.2, 1H), 7.59 (d, J=8.2, 1H), 7.61 (s, 1H), 9.84 (s, 1H).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-98e32560df2347879b6cdab0ddc7f7d3
Source dataset
uspto-grants-2007_04
Patent number
US07199142B2

Reaction notes

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