Triphenylphosphine → HCID 53629680, compound

HRID 1990016Notes

Reaction equation

HRID 1990016 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[O:20]1[CH2:25][CH2:24][CH:23](O)[CH2:22][CH2:21]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.C(OCC)(=O)C.CCCC(C)C>[C:14]1([CH2:13][O:12][C:10]2[CH:9]=[C:4]([CH:3]=[C:2]([O:1][CH:23]3[CH2:24][CH2:25][O:20][CH2:21][CH2:22]3)[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 5462977Diethyl azodicarboxylateHCID 7472028Methyl 3-(benzyloxy)-5-hydroxybenzoate

Product 1

HCID 53629680HCID 53629680, compoundYield 87.6%

Reagents, catalysts & solvents 3

HCID 78922-MethylpentaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

Methyl 3-hydroxy-5-{[phenylmethyl]oxy}benzoate (7.75 g, 30.0 mmol), tetrahydro-4H-pyran-4-ol (4.28 mL, 45.0 mmol) and triphenylphosphine (11.8 g, 45.0 mmol) were stirred under argon in THF (166 mL) and cooled to 5° C. in an ice bath. DEAD (19.6 mL, 45.0 mmol) was added dropwise to the mixture, maintaining the internal temperature below 10° C. Stirring was continued for 16 hours then the reaction mixture reduced in vacuo and the residue redissolved in ethyl acetate (60 mL) and isohexane (60 mL). The precipitate was removed, the filtrate concentrated in vacuo and purified by chromatography on silica, eluting with 0-25% ethyl acetate in isohexane (a small quantity of DCM used to assist column loading), to give the desired compound as a colourless oil (9.0 g).

Workup

  1. temperaturemaintaining the internal temperature below 10° C
  2. customThe precipitate was removed
  3. concentrationthe filtrate concentrated in vacuo
  4. custompurified by chromatography on silica
  5. washeluting with 0-25% ethyl acetate in isohexane (a small quantity of DCM

Sources & evidence

ORD record
ord-2fdc6646dae04610943e149b864ba2db
Source dataset
uspto-grants-2010_01
Patent number
US07642263B2

Reaction notes

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