Hydrochloric Acid → HCID 53815595, compound

HRID 356580Notes

Reaction equation

HRID 356580 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:21]([O-:23])=[O:22])=[C:17]([CH:20]=1)[CH:18]=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:24]([Mg]Br)=[CH2:25].Cl>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([N+:21]([O-:23])=[O:22])=[C:17]([CH:18]([OH:19])[CH:24]=[CH2:25])[CH:20]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18938756HCID 18938756, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 53815595HCID 53815595, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-[3'-(t-Butyidimethylsilyloxy)propyloxy]-2-nitrobenzaldehyde (5.80 g) is dissolved in dry THF (35 ml), and thereto is added with stirring vinyl-magnesium bromide (1.7 equivalent) in THF solution in a dry ice-acetone bath. The mixture is stirred for two hours, and thereto is added 5% hydrochloric acid (30 ml). The mixture is stirred at room temperature, extracted with ethyl acetate, and purified by silica gel column chromatography to give 1-{5'-[3"-(t-butyldimethylsilyloxy)propyloxy]-2'-nitrophenyl}-2-propen-1-ol (5.02 g).

Workup

  1. stirringThe mixture is stirred at room temperature
  2. extractionextracted with ethyl acetate
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f418313f0f44022a0db7d495c5c11be
Source dataset
uspto-grants-1998_11
Patent number
US05837673

Reaction notes

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