Triphenylphosphine → HCID 68726283, compound

HRID 493191Notes

Reaction equation

HRID 493191 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:9]=2[C:10]=1[CH:11]([CH3:13])[CH3:12])=[O:5])[CH3:2].[CH:19]([N:22]1[CH2:27][CH2:26][CH:25](O)[CH2:24][CH2:23]1)([CH3:21])[CH3:20].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>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:17]=[C:16]([O:18][CH:25]3[CH2:26][CH2:27][N:22]([CH:19]([CH3:21])[CH3:20])[CH2:23][CH2:24]3)[CH:15]=[CH:14][C:9]=2[C:10]=1[CH:11]([CH3:13])[CH3:12])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 796811-Isopropylpiperidin-4-olHCID 5363146Diisopropyl azodicarboxylateHCID 68725520HCID 68725520, compound

Product 1

HCID 68726283HCID 68726283, compoundYield 119.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The above prepared 6-hydroxy-3-isopropyl-benzofuran-2-carboxylic acid ethyl ester (0.400 g, 1.61 mmol) was dissolved in 8 mL of THF and treated successively at 0° C. with 1-isopropyl-piperidin-4-ol (0.461 g, 2 eq.), triphenylphosphine (0.845 g, 2 eq.) and DIAD (0.630 mL, 2 eq.), and the mixture then kept at ambient temperature for another 1 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, NEt3/AcOEt=5/95), yielded 0.720 g of the title compound as light yellow oil, contaminated with tiny amounts of reduced DIAD.

Workup

  1. additionPouring
  2. extractionice, twofold extraction with AcOEt
  3. washwashing with water
  4. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-87f0d5cdc3704b898d6d87630fb1d157
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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