Sodium Thiosulfate → HCID 59248869, compound

HRID 2386198Notes

Reaction equation

HRID 2386198 reaction equation
[I:1][C:2]1[O:6][C:5]([CH:7]([OH:22])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[N:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[I:1][C:2]1[O:6][C:5]([C:7](=[O:22])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68527740HCID 68527740, compound

Product 1

HCID 59248869HCID 59248869, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Anhydrous dichloromethane (2 mL) was used to solubilize 1-(5-iodooxazol-2-yl)-7-(3-methoxyphenyl)heptan-1-ol (0.050 g, 0.120 mmol) under an atmosphere of argon with stirring. Dess-Martin periodinane (0.076 g, 0.181 mmol) was added and the reaction was allowed to proceed over 1 hour at ambient temperature. The reaction was then worked up with saturated sodium bicarbonate. Saturated sodium thiosulfate was added and the organic phase was separated. The organic phase was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the product (60%, 0.030 g) was purified by preparative thin layer chromatography with silica (30% ethyl acetate:hexanes mobile phase) as a yellow oil: 1H NMR (600 MHz, CDCl3) δ 7.33 (s, 1H), 7.18 (m, 1H), 6.75 (d, J=7.2 Hz, 1H), 6.71 (m, 2H), 3.79 (s, 3H), 3.02 (t, 2H), 2.57 (t, 3H), 1.71-1.76 (m, 2H), 1.60-1.65 (m, 2H), 1.35-1.44 (m, 4H); 13C NMR (150 MHz, CDCl3) δ 187.11, 162.53, 159.53, 144.27, 137.40, 129.15, 120.80, 114.12, 110.85, 93.61, 55.09, 38.63, 35.87, 31.09, 28.91 (2 C), 23.75; HRMS (ES+) m/e calc'd for [M+H]+ C17H21INO3: 414.0561. found 414.0560.

Workup

  1. customthe organic phase was separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe product (60%, 0.030 g) was purified by preparative thin layer chromatography with silica (30% ethyl acetate:hexanes mobile phase) as a yellow oil

Sources & evidence

ORD record
ord-1455b5f4b4e44ecdb7a135dc9607464b
Source dataset
uspto-grants-2012_09
Patent number
US08268817B2

Reaction notes

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