Methanol → HCID 68677761, compound

HRID 639738Notes

Reaction equation

HRID 639738 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10](=[O:23])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH:21]=[CH2:22])[CH:14]=1.[C:24]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:24][O:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10](=[O:23])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH:21]=[CH2:22])[CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 136368373HCID 136368373, compound

Product 1

HCID 68677761HCID 68677761, compoundYield 5.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 20 ml of tetrahydrofuran were added 2.00 g of 4-hydroxy-3-[3-(3-allyloxyphenyl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one, 1.85 g of triphenylphosphine and 0.23 g of methanol, and to the mixture was added dropwise a solution of 1.23 g of diethyl azodicarboxylate in 12 ml of tetrahydrofuran. The mixture was stirred at room temperature for 18 hours, and the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.12 g of 4-methoxy-3-[3-(3-allyloxyphenyl)-1-oxo-2-propenyl]-6-methyl-2H-pyran-2-one [Compound No. (5a)] as a yellow oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-99ba8e4926564f249f2e816dba7bcb3c
Source dataset
uspto-grants-2010_04
Patent number
US07691883B2

Reaction notes

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