Tetrahydrofuran → HCID 54490614, compound

HRID 981142Notes

Reaction equation

HRID 981142 reaction equation
C([Li])CCC.[CH3:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([CH3:18])[C:14]=1[N+:15]([O-:17])=[O:16])[CH:10]=O.[Cl-].[NH4+].[CH2:21]1C[O:24][CH2:23][CH2:22]1>>[CH3:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:21][CH2:22][CH2:23][OH:24])[CH:12]=[C:13]([CH3:18])[C:14]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 126541443,5-Dimethyl-4-nitrobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 54490614HCID 54490614, compound

Procedure

To a stirred suspension of 3-(hydroxypropyl)triphenylphosphonium bromide (10.5 g) in dry THF (100 ml) at 0°, under nitrogen was added n-butyllithium (1.8 M in hexane, 30 ml). The stirring was continued at 0° for 30 min then a solution of 3,5-dimethyl-4-nitrobenzaldehyde (4.5 g) in dry THF (50 ml) was added over 10 min. The mixture was stirred at -10° for 1 h and at 0° for 1 h, saturated ammonium chloride (50 ml) was added and the mixture was extracted with EA (3×50 ml) the organic extracts were washed with water, brine, dried, concentrated and purified by [FCS] (triethylamine deactivated silica) eluting with EA-methanol (9:1) gave the title compound (0.3 g). T.l.c. (Toluene:ethanol:0.88 ammonia solution 39:10:1) Rf 0.18.

Workup

  1. extractionthe mixture was extracted with EA (3×50 ml) the organic extracts
  2. washwere washed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. custompurified by [FCS] (triethylamine deactivated silica)
  6. washeluting with EA-methanol (9:1)

Sources & evidence

ORD record
ord-dc8b4d4c45bd4688be450146ce779c77
Source dataset
uspto-grants-1991_02
Patent number
US04990505

Reaction notes

Loading…