Triphenylphosphine → HCID 131726478, compound

HRID 2240145Notes

Reaction equation

HRID 2240145 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 up 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-87e5446cc09a494e8360ba33f162d19c
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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