Acetone → HCID 53636236, compound

HRID 1906683Notes

Reaction equation

HRID 1906683 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([C@@H:27]2[C@:44]3([CH3:45])[C@H:30]([C@H:31]4[C@H:41]([CH2:42][CH2:43]3)[C@:39]3([CH3:40])[C:34]([CH2:35][C@@H:36]([O:53][CH:54]5[CH2:59][CH2:58][CH2:57][CH2:56][O:55]5)[CH2:37][C@@H:38]3[O:46][CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][O:48]3)=[CH:33][CH2:32]4)[CH2:29][CH2:28]2)[CH2:14][CH2:15][C@@H:16]([F:26])[C:17]([O:20][CH:21]([O:23][CH2:24][CH3:25])[CH3:22])([CH3:19])[CH3:18])(=O)=O)=CC=1.[I-:60].[Na+].CC(C)=O.O>C(Cl)Cl>[O:48]1[CH2:49][CH2:50][CH2:51][CH2:52][CH:47]1[O:46][C@@H:38]1[C@@:39]2([CH3:40])[C:34](=[CH:33][CH2:32][C@@H:31]3[C@@H:41]2[CH2:42][CH2:43][C@@:44]2([CH3:45])[C@H:30]3[CH2:29][CH2:28][C@@H:27]2[C@H:13]([CH2:12][I:60])[CH2:14][CH2:15][C@@H:16]([F:26])[C:17]([O:20][CH:21]([O:23][CH2:24][CH3:25])[CH3:22])([CH3:19])[CH3:18])[CH2:35][C@@H:36]([O:53][CH:54]2[CH2:59][CH2:58][CH2:57][CH2:56][O:55]2)[CH2:37]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 5238Sodium IodideHCID 13826515HCID 13826515, compound

Product 1

HCID 53636236HCID 53636236, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.223 g. (0.00026 mole) of [1α,3β,24R]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-en-21-ol 21-(4-methylbenzenesulfonate), and 0.150 g. (0.0010 mole) of sodium iodide in 2 ml. of acetone was heated at 50° for 18 hr and cooled. The mixture was poured into water and the product was isolated with methylene chloride. The organic layers were washed with aqueous sodium sulfite solution, and saturated aqueous sodium bicarbonate solution. The organic layers were dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to yield [1α,3β,24R]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluoro-21-iodocholest-5-ene.

Workup

  1. additionA mixture of 0.223 g
  2. temperaturecooled
  3. washThe organic layers were washed with aqueous sodium sulfite solution, and saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e23410b54e2d4668ab94b83c39d4dbd1
Source dataset
uspto-grants-1987_03
Patent number
US04652405

Reaction notes

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