Triphenylphosphine → HCID 68861618, compound

HRID 1726030Notes

Reaction equation

HRID 1726030 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C@@H:14]1[CH2:19][CH2:18][O:17][C:15]1=[O:16].[F:20][C:21]([F:30])([F:29])[C:22]1[CH:27]=[CH:26][C:25](O)=[CH:24][CH:23]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:20][C:21]([F:30])([F:29])[C:22]1[CH:27]=[CH:26][C:25]([O:13][C@H:14]2[CH2:19][CH2:18][O:17][C:15]2=[O:16])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 71570702-Hydroxy-gamma-butyrolactone, (2R)-

Product 1

HCID 68861618HCID 68861618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl azodicarboxylate (2.31 ml, 14.7 mmol) is slowly added to a solution of (R)-(+)-α-hydroxy-γ-butyrolactone (1 g, 9.8 mmol), 4-trifluoromethylphenol (1.58 g, 9.8 mmol) and triphenylphosphine (3.86 g, 14.7 mmol) in anhydrous THF (80 ml) cooled to 0° C. After stirring for 5 minutes at 0° C. and overnight at room temperature, the solvent is evaporated off and the triphenylphosphine oxide is then precipitated from ether and filtered off. The filtrate is then washed with water, dried over magnesium sulphate and evaporated. After purification by flash chromatography (3/1 heptane/EtOAc), the expected compound is obtained in the form of a white powder (1.14 g, 47%).

Workup

  1. customthe solvent is evaporated off
  2. customthe triphenylphosphine oxide is then precipitated from ether
  3. filtrationfiltered off
  4. washThe filtrate is then washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customAfter purification by flash chromatography (3/1 heptane/EtOAc)

Sources & evidence

ORD record
ord-f5305853c77b46af92a88b72da9060e3
Source dataset
uspto-grants-2009_02
Patent number
US07491747B2

Reaction notes

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