Triphenylphosphine → HCID 131726478, compound

HRID 1727129Notes

Reaction equation

HRID 1727129 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[OH:12][C@H:13]1[CH2:17][CH2:16][O:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[C:3]([O:12][C@@H:13]2[CH2:17][CH2:16][O:15][CH2:14]2)[CH:2]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 12127IsovanillinHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Product 1

HCID 131726478HCID 131726478, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
5 °C

Procedure

3-Hydroxy-4-methoxybenzaldehyde (7.6 g; 50 mmol) was dissolved in THF (200 mL) followed by addition of (S)-3-hydroxytetrahydrofuran (6.0 mL; 75 mmol) and triphenylphosphine (19.7 g; 75 mmol). The resulting solution was cooled to 5° C. and diisopropyl azodicarboxylate (14.8 mL; 75 mmol) was added dropwise over 10 minutes. The clear orange solution was stirred at ambient temperature for 16 hours. Thin layer chromatography analysis using a 1:1 mixture of hexane/ethyl acetate determined the reaction to be complete. The solvent was removed under reduced pressure and the residue was taken in ethyl acetate (60 mL) and extracted twice with 20% aqueous sodium bisulfite (150 mL/extraction). The extracts were pooled and washed with ethyl acetate (75 mL). The aqueous layer was basified with solid sodium hydroxide (26 g) and then extracted with 3×150 mL of ethyl acetate (150 mL/extraction). The organic extracts were pooled, washed with 40 mL of brine, dried (Na2SO4), and concentrated to afford 7.4 g (66%) of a pale yellow oil. 1H NMR (CDCl3; 300 MHz) δ 2.2-2.4 (m, 2H); 3.8-4.1 (m, 7H); 5.0 (m, 1H); 7.0 (d, 1H); 7.4 (s, 1H); 7.5 (d, 1H); 9.9 (s, 1H). ES-MS [M+H]+=223.2

Workup

  1. customthe reaction
  2. customThe solvent was removed under reduced pressure
  3. extractionextracted twice with 20% aqueous sodium bisulfite (150 mL/extraction)
  4. washwashed with ethyl acetate (75 mL)
  5. extractionextracted with 3×150 mL of ethyl acetate (150 mL/extraction)
  6. washwashed with 40 mL of brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6d03d9e1b506427594a6370edbfb01cb
Source dataset
uspto-grants-2009_02
Patent number
US07495017B2

Reaction notes

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