Iodine → HCID 67650750, compound

HRID 1600150Notes

Reaction equation

HRID 1600150 reaction equation
[C:1]1([CH2:7][O:8][CH:9]([CH2:14][CH:15]=[CH2:16])[CH:10]([OH:13])[CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].[I:22]I.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)C.O>[I:22][CH2:16][C@H:15]1[O:13][C@H:10]([CH2:11][OH:12])[C@@H:9]([O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:14]1

Participants

7

Reactant 4

HCID 807IodineHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 13119197HCID 13119197, compound

Product 1

HCID 67650750HCID 67650750, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of 4.5 g of product from Example 333 in 77.8 ml of diethyl ether and 25.5 ml of water is treated with 2.58 g of solid sodium bicarbonate followed by 7.6 g of iodine. The reaction is stirred for 3 hours at 0° C. then at room temperature overnight. The mixture is cooled to 0° C. and sodium sulfite is added until the reaction is colorless. The solution is extracted with diethyl ether, dried and concentrated in vacuo to give 7.0 g of an oil. The oil is purified by chromatography (Silica gel: 5% diethyl ether/hexane) to give 2.8 g of Isomer A and 1.86 g of Isomer B. Isomer A:

Workup

  1. customat room temperature
  2. customovernight
  3. temperatureThe mixture is cooled to 0° C.
  4. extractionThe solution is extracted with diethyl ether
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92b33441fd90496a8ba46800a6d6c5be
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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