2-Iodobenzoic acid → (6S)-7-(4-fluorophenoxy)-6-hydroxyheptanal

HRID 2304126Notes

Reaction equation

HRID 2304126 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][C@@H:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:4][CH:3]=1.IC1C=CC=CC=1C(O)=O>C1COCC1.CS(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C@@H:8]([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 69412-Iodobenzoic acidHCID 59971312(6S)-7-(4-fluorophenoxy)-heptane-1,6-diol

Product 1

HCID 59064024(6S)-7-(4-fluorophenoxy)-6-hydroxyheptanalYield 61.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6S)-7-(4-fluorophenoxy)-heptane-1,6-diol (3.6 g, 14.8 mmol) in dry THF (60 ml) was added dropwise a solution of 2-iodobenzoic acid (5 g, 17.8 mmol) in dry DMSO (4 ml) over a period of 25 minutes at room temperature. After 15 minutes the reaction mixture was decomposed with crushed ice, filtered through celite and concentrated. The residue was extracted with ethylether, washed with brine, dried over Na2SO4 and the organic solvent was removed under reduced pressure. The residue was purified by silica gel chromatography using EtOAc-hexane (1:9) to give (6S)-7-(4-fluorophenoxy)-6-hydroxy-heptanal (2.2 g, 61.6%); [α]D+12 (c 3.8, CHCl3), 1H-NMR (CDCl3, 200 Hz): δ 1.4-1.8 (m, 6H), 2.49 (dt, 2H), 3.71-4.05 (m, 4H), 6.782-7.02 (m, 4H), 9.8 (s, 1H); HRMS (FAB): calcd. for C13H17O3F (M+) 240.116173 found 240.116465.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated
  3. extractionThe residue was extracted with ethylether
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customthe organic solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c46b896c2b9440158db84fdf46307a7c
Source dataset
uspto-grants-2002_08
Patent number
US06433197B1

Reaction notes

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