Diethyl Ether → HCID 86743645, compound

HRID 329534Notes

Reaction equation

HRID 329534 reaction equation
[OH:1][N:2]=[C:3]([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12]([CH2:13][C@@H:14]([O:24][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[CH2:15][CH2:16]2)=[CH:11][CH:10]=3)[CH2:7][CH2:6]1)[CH3:4].[H-].[Na+].[CH3:33][C:34]1([O:37][CH2:36]1)[CH3:35].C(OCC)C>CN(C)C=O>[OH:37][C:34]([CH3:36])([CH3:35])[CH2:33][O:1][N:2]=[C:3]([C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C:9]3[C@H:19]([CH2:20][CH2:21]2)[C@:17]2([CH3:18])[C:12]([CH2:13][C@@H:14]([O:24][CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][O:26]4)[CH2:15][CH2:16]2)=[CH:11][CH:10]=3)[CH2:7][CH2:6]1)[CH3:4]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11208Isobutylene oxideHCID 24758Sodium hydrideHCID 86743646HCID 86743646, compound2×

Product 1

HCID 86743645HCID 86743645, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A portion (606 mg) of the 20-hydroxyimino-3β-(2-tetrahydropyranyloxy)-5,7-pregnadiene obtained in (a) was dissolved in 10 ml of dry dimethylformamide, and after addition of 100 mg of sodium hydride (60% in oil), the solution was vigorously stirred for 30 minutes at room temperature. After addition of 0.5 ml of isobutylene oxide, the mixture was heated on an oil bath (80°-100° C.) for 1 hour. After cooling, diethyl ether was added, and the mixture was washed with water and dried, followed by the distilling off of the solvent under vacuum. The residue was subjected to silica gel column chromatography to obtain 271 mg of 20-(2-hydroxy-2-methylpropyloxyimino)-3β-(2-tetrahydropyranyloxy)-5,7pregnadiene.

Workup

  1. temperaturethe mixture was heated on an oil bath (80°-100° C.) for 1 hour
  2. temperatureAfter cooling
  3. washthe mixture was washed with water
  4. customdried

Sources & evidence

ORD record
ord-9c40b691f0f343a5bece15a75c0da850
Source dataset
uspto-grants-1990_01
Patent number
US04891364

Reaction notes

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