Triphenylphosphine → 1,1-Dimethylethyl 2,5-dihydro-3-furancarboxylate

HRID 1361295Notes

Reaction equation

HRID 1361295 reaction equation
O[CH:2]1[CH2:6][O:5][CH2:4][CH:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[O:5]1[CH2:6][CH:2]=[C:3]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 114128161,1-Dimethylethyl tetrahydro-4-hydroxy-3-furancarboxylate2×

Product 1

HCID 112060181,1-Dimethylethyl 2,5-dihydro-3-furancarboxylateYield 51.34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

The product of Step B, t-butyl 4-hydroxytetrahydrofuran-3-carboxylate (0.83 g, 4.41 mmol) and PPh3 (1.74 g, 6.63 mmol) were placed in THF (5 mL), the solution was cooled to 0-5° C., and DIAD (1.13 mL, 5.74 mmol) was added dropwise. After reacting at rt for 12 h, the reaction mixture was filtered, washed with a solution of EtOAc/Hex=1/4, and the filtrate concentrated in vacuo The residue was purified by column chromatography (eluent, EtOAc/Hex=1/7) to give the title compound (0.39 g, 51.34%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washwashed with a solution of EtOAc/Hex=1/4
  3. concentrationthe filtrate concentrated in vacuo The residue
  4. customwas purified by column chromatography (eluent, EtOAc/Hex=1/7)

Sources & evidence

ORD record
ord-691e1cfd71c24767b82416dafd604112
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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