Sodium Thiosulfate → HCID 86627924, compound

HRID 2240978Notes

Reaction equation

HRID 2240978 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[C:8](/[CH3:12])=[CH:9]/[CH2:10]O)[CH:5]=[CH:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:15].C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[CH:9][CH3:10])[CH:12]=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59305352HCID 59305352, compound

Product 1

HCID 86627924HCID 86627924, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (E)-3-(3-bromophenyl)-but-2-en-1-ol (1.03 g, 4.54 mmol) in DCM (10 mL) at 0 deg C., was added Dess-Martin periodinane (2.11 g, 5 mmol). The resulting suspension was warmed to 23° C. and stirred for approx. 30 min. until the reaction was complete by TLC. The mixture was poured into 50 mL of saturated aqueous NaHCO3, containing Na2S2O3 (1 g). This mixture was stirred vigorously until both layers became clear. The aqueous layer was extracted with DCM (2×) and the combined organic layers were dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by flash chromatography (10% EtOAc/hexanes) to afford the titled compound as a white solid (910 mg, 89% yield) that was a 5:1 ratio of E:Z isomers.

Workup

  1. customat 0 deg C
  2. stirringThis mixture was stirred vigorously until both layers
  3. extractionThe aqueous layer was extracted with DCM (2×)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b885800377a14f1f9a08fbcbd928d276
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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