Sodium Bicarbonate → HCID 70060789, compound

HRID 1594942Notes

Reaction equation

HRID 1594942 reaction equation
[CH3:1][O:2][C:3]1[C:12](I)=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:14]#[N:15])=[CH:10]2)=[CH:5][CH:4]=1.[CH2:16]([OH:21])/[CH:17]=[CH:18]\[CH2:19][OH:20].C([O-])(O)=O.[Na+]>CN1CCCC1=O.Cl[Pd]Cl>[CH3:1][O:2][C:3]1[C:12]([C:17]([CH2:16][OH:21])=[CH:18][CH2:19][OH:20])=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:14]#[N:15])=[CH:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 6437902-Butene-1,4-diol, (2Z)-HCID 21707103HCID 21707103, compound

Product 1

HCID 70060789HCID 70060789, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of Example 53B (3.09 g, 10 mmol), PdCl2 (120 mg, 1 mmol), cis-2-butene-1,4-diol (1.23 mL, 15 mmol) and NaHCO3 (1.01 g, 12 mmol) in N-methylpyrrolidinone (10 mL) was stirred at 130° C. for 1 h, cooled to room temperature and chromatographed on silica gel with 30% ethyl acetate/hexanes to provide 2.19 g of the title compound as a mixture of diastereomers.

Workup

  1. customchromatographed on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2683099e7855465283656896d8ddaa89
Source dataset
uspto-grants-2001_09
Patent number
US06284796B1

Reaction notes

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