Triphenylphosphine → HCID 68867952, compound

HRID 1988225Notes

Reaction equation

HRID 1988225 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([OH:6])=[O:5].O[CH:16]([CH2:18][CH2:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[CH3:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(OCC)C>[CH3:17][CH:16]([O:5][C:4](=[O:6])[C:3]1[C:7]([O:13][CH3:14])=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:2]=1[OH:1])[CH2:18][CH2:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 766564,6-Dimethoxysalicylic acidHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 85830276HCID 85830276, compound

Product 1

HCID 68867952HCID 68867952, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-hydroxy-4,6-dimethoxy-benzoic acid (0.36 g, 0.18 mmol), 2-hydroxy-dec-9-en-5-one (0.024 g, 0.14 mmol), PPh3 (0.042 g, 0.16 mmol), diethyl azodicarboxylate (25 μL, 0.15 mmol) in diethyl ether (1.5 mL) was stirred at room temperature for 7 hours. Concentration under vacuum and chromatography afforded 2-hydroxy-4,6-dimethoxy-benzoic acid 1-methyl-4-oxo-non-8-enyl ester as a light yellow oil (32 mg).

Workup

  1. concentrationConcentration under vacuum and chromatography

Sources & evidence

ORD record
ord-22e88514cf8d4bcdbc8eca51f58507b0
Source dataset
uspto-grants-2009_06
Patent number
US07553979B2

Reaction notes

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