Sodium Thiosulfate → HCID 68541511, compound

HRID 1444758Notes

Reaction equation

HRID 1444758 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O:23]1[CH:27]=[N:26][N:25]=[C:24]1[CH:28]([OH:46])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].[O-]S([O-])(=S)=O.[Na+].[Na+].CO.C(Cl)Cl>C(Cl)Cl.CCOCC.C([O-])(O)=O.[Na+]>[O:23]1[CH:27]=[N:26][N:25]=[C:24]1[C:28](=[O:46])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 21226129Dichloromethane methanolHCID 68541394HCID 68541394, compound

Product 1

HCID 68541511HCID 68541511, compoundYield 76.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

(140) A suspension of the Dess-Martin periodinane (1.2 equiv, 0.025 mmol, 11 mg) in anhydrous CH2Cl2 (0.5 mL) was treated with a solution of 1-([1,3,4]oxadiazol-2-yl)octadec-9-en-1-ol (7 mg, 0.021 mmol) in anhydrous CH2Cl2 (0.5 mL) at rt under N2. After 6 h the suspension was diluted with Et2O (10 mL), and poured into a solution of Na2S2O3 (77 mg) in saturated aqueous NaHCO3 (6.5 mL). The mixture was stirred at rt for 1 h and the layers were separated. The ethereal layer was washed with saturated aqueous NaHCO3 (1×10 mL) and H2O (1×10 mL), dried (MgSO4), filtered and evaporated. Flash chromatography (SiO2, 1.5 cm×15 cm, 2% MeOH—CH2Cl2) afforded 1-([1,3,4]oxadiazol-2-yl)octadec-9-en-1-one (140) (5 mg, 0.016 mmol, 75% yield) as a dark yellow oil: 1H NMR (CDCl3, 250 MHz) d 9.34 (s, 1H), 5.42-5.26 (m, 2H), 3.04 (t, J=7.4 Hz, 2H), 2.12-1.87 (m, 4H), 1.82-1.75 (m, 2H), 1.43-1.19 (m, 20H), 0.88 (br t, J=6.8 Hz, 3H); IR (CDCl3)umax 2940, 2860, 1705, 1612, 1547, 1510, 1423, 1380 cm−1; MALDI-FTMS (DHB) m/z 335.2689 (C20H34N2O2+H+ requires 335.2698).

Workup

  1. customthe layers were separated
  2. washThe ethereal layer was washed with saturated aqueous NaHCO3 (1×10 mL) and H2O (1×10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7fe865a41a514d6d8607c585f9476e14
Source dataset
uspto-grants-2010_02
Patent number
US07662971B2

Reaction notes

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