Hexane → HCID 17937806, compound

HRID 1828650Notes

Reaction equation

HRID 1828650 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][C:8](=[O:9])[C:4]=2[CH:3]=1.[CH3:12]OC(OC)OC.C([O-])(O)=O.[Na+].CCCCCC>CO.C(O)C.C(OCC)(=O)C>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH:7]=[C:8]([O:9][CH3:12])[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 8058HexaneHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 99641425-Hydroxy-1-benzofuran-3(2H)-one

Product 1

HCID 17937806HCID 17937806, compoundYield 73.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

900 mg (6.0 mmol) XVIII, 788 μl (7.2 mmol) orthoformic acid trimethyl ester and 57 mg (0.3 mmol) p-toluenesulfonic aid monohydrate were heated under reflux for 12 h in 70 ml methanol. The reaction was stopped by addition of saturated NaHCO3 solution and the solvent was removed. Subsequent flash chromatography (100 g SiO2, n-hexane:ethyl acetate=2:1, applied with ethanol) yielded 717 mg (4.4 mmol, 73%) XXI.

Workup

  1. customthe solvent was removed

Sources & evidence

ORD record
ord-673a2acdc8c74e29a32ceda6da735d58
Source dataset
uspto-grants-2006_06
Patent number
US07060109B2

Reaction notes

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