Sodium Iodide → HCID 56610066, compound

HRID 1589122Notes

Reaction equation

HRID 1589122 reaction equation
[C:1]([O:4][C@@H:5]1[C@@:35]2([CH3:36])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:37])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:30])[CH2:18]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:8][C@@H:7]([O:38][C:39](=[O:41])[CH3:40])[CH2:6]1)(=[O:3])[CH3:2].[I-:42].[Na+]>C1(C)C=CC=CC=1.[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.O>[C:1]([O:4][C@@H:5]1[C@@:35]2([CH3:36])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:34]2[CH2:33][CH2:32][C@@:31]2([CH3:37])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:30])[CH2:18][I:42])[CH2:8][C@@H:7]([O:38][C:39](=[O:41])[CH3:40])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 5238Sodium IodideHCID 12790113HCID 12790113, compound

Product 1

HCID 56610066HCID 56610066, compoundYield 97.5%

Reagents, catalysts & solvents 3

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Second process. A solution of 23.4 g of (20S)-1α,3β-diacetoxy-20-methyl-21-p-toluenesulphonyloxy-pregn-5-ene in 260 ml of toluene is treated with 1.04 g of hexadecyl-tri-n-butyl-phosphonium bromide and a solution of 132 g of sodium iodide in 260 ml of water and the mixture is heated under reflux for 5 hours. After cooling, the organic phase is separated, washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated at 30°/11 Torr. Chromatography of the residue on 270 g of silica gel with hexane/ether (19:1 and 9:1) gives 21.1 g of product of melting point 135°-136°. After recrystallization from concentrated pentane solution, there are obtained 16.0 g of product of melting point 136°; [α]D20 =-11.0° (c=1.0 in CHCl3).

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter cooling
  3. customthe organic phase is separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated at 30°/11 Torr

Sources & evidence

ORD record
ord-94023ee3c23c4323a3b3be00f98f9a4a
Source dataset
uspto-grants-1986_02
Patent number
US04568491

Reaction notes

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