Triphenylphosphine → HCID 12050295, compound

HRID 993420Notes

Reaction equation

HRID 993420 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.O[C@@H:12]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([O:15][CH3:16])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][C@H:12]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[C:4]([Cl:10])[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 185874-Bromo-2,6-dichlorophenolHCID 5289077(S)-methyl 2-hydroxy-3-phenylpropanoateHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 12050295HCID 12050295, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-2,6-dichlorophenol (1.24 g, 6.02 mmol), methyl (2S)-2-hydroxy-3-phenylpropanoate (1.30 g, 7.22 mmol) and triphenylphosphine (2.05 g, 7.83 mmol) in THF (13 mL) at room temperature was treated with DEAD (1.28 mL, 8.13 mmol), stirred for 2 hours, and concentrated. The concentrate was triturated with 10% ethyl acetate/hexanes, filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes to provide 1.90 g (78%) of the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was triturated with 10% ethyl acetate/hexanes
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-58ef29c1a2a141568d6d4a821d3c0c8f
Source dataset
uspto-grants-2002_10
Patent number
US06472545B2

Reaction notes

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