Triphenylphosphine → HCID 58551520, compound

HRID 2204172Notes

Reaction equation

HRID 2204172 reaction equation
[O:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.O[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[O:18][CH3:19].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>[CH3:19][O:18][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:8]=1[O:6][C@@H:3]1[CH2:4][CH2:5][O:1][CH2:2]1)[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 19844Methyl VanillateHCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 58551520HCID 58551520, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3S)-tetrahydrofuran-3-ol (403 mg, 4.57 mmol), methyl 4-hydroxy-3-methoxy-benzoate (1.00 g, 5.49 mmol) and triphenylphosphane (1.44 g, 1.27 mL, 5.49 mmol) in THF (13 mL) at 0° C. was added DIAD (1.11 g, 1.06 mL, 5.49 mmol). The ice bath was removed and the reaction mixture was stirred at room temperature for 16 h, then at 55° C. for 4 h. The mixture was diluted with EtOAc and was washed with sat. aq. NaHCO3 (×2) and brine (×2). The organic layer was dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane) to yield (R)-methyl 3-methoxy-4-(tetrahydrofuran-3-yloxy)benzoate (0.97 g, 84%) as a viscous liquid. ESI-MS m/z calc. 252.1, found 253.3 (M+1)+; Retention time: 1.72 minutes (3 min run).

Workup

  1. customThe ice bath was removed
  2. waitat 55° C. for 4 h
  3. additionThe mixture was diluted with EtOAc
  4. washwas washed with sat. aq. NaHCO3 (×2) and brine (×2)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3f49a4f13d6b46ae9e84598a6176ea00
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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