1-Butanol → HCID 22277858, compound

HRID 1063884Notes

Reaction equation

HRID 1063884 reaction equation
[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[I:13].[CH2:14](O)[CH2:15][CH2:16][CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:14]([O:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[I:13])[CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 11776TriphenylphosphineHCID 1494374HCID 1494374, compoundHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22277858HCID 22277858, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 4-hydroxy-3-iodo-5-nitrobenzaldehyde (3.16 g, 10.7 mmol) in THF (100 ml) was added n-butanol (1.94 ml, 21.5 mmol), triphenyl phosphine (3.10 g, 11.8 mmol) and diethylazodicarboxylate (1.85 ml, 11.8 mmol). The mixture was stirred 18 h then filtered and all volatiles removed the residue was chromatographed on silica to afford the title compound (2.74 g, 73%).). 1H NMR (400 MHz, CDCl3) δ 9.94 (s, 1H), 8.54 (d, j=2.0 Hz, 1H), 8.28 (d, j=2.0 Hz, 1H), 4.18 (t, j=6.5, 2H), 1.86-1.94 (m, 2H), 1.52-1.61 (m, 2H), 1.01 (t, j=7.1 Hz, 3H). M+1=350.

Workup

  1. filtrationthen filtered
  2. customall volatiles removed the residue
  3. customwas chromatographed on silica

Sources & evidence

ORD record
ord-f57687c3c302453c90c3025d67c161a4
Source dataset
uspto-grants-2005_11
Patent number
US06967220B2

Reaction notes

Loading…