1-Bromo-3-methylbutane → 1alpha,3beta-Bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-ol

HRID 1708828Notes

Reaction equation

HRID 1708828 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH:3]([CH3:5])[CH3:4].C(Br)CC(C)C.[Mg].[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:21][C@@H:22]1[C@@:42]2([CH3:43])[C:26](=[CH:27][CH:28]=[C:29]3[C@@H:41]2[CH2:40][CH2:39][C@@:38]2([CH3:44])[C@H:30]3[CH2:31][CH2:32][C@@H:33]2[CH:34]([CH:36]=[O:37])[CH3:35])[CH2:25][C@@H:24]([O:45][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][O:47]2)[CH2:23]1.[OH-].[Na+]>O1CCCC1>[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:21][C@@H:22]1[C@@:42]2([CH3:43])[C:26](=[CH:27][CH:28]=[C:29]3[C@@H:41]2[CH2:40][CH2:39][C@@:38]2([CH3:44])[C@H:30]3[CH2:31][CH2:32][C@@H:33]2[C@H:34]([CH3:35])[CH:36]([OH:37])[CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])[CH2:25][C@@H:24]([O:45][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][O:47]2)[CH2:23]1

Participants

7

Reactant 5

HCID 78911-Bromo-3-methylbutaneHCID 14798Sodium HydroxideHCID 5462224MagnesiumHCID 228438971alpha, 3beta-Bis(tetrahydropyran-2-yloxy)pregna-5,7-diene-20-carbaldehydeHCID 178418529HCID 178418529, compound

Product 1

HCID 228438951alpha,3beta-Bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-olYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 20 ml of a tetrahydrofuran solution of the isoamylmagnesium bromide prepared from 2.27 g of isoamyl bromide and 0.48 g of magnesium was slowly added a solution of 5.12 g of 1α,3β-bis(tetrahydropyran-2-yloxy)pregna-5,7-diene-20-carbaldehyde in 30 ml of tetrahydrofuran under ice-cooling. After the addition, the mixture was further stirred at 0° C. for 1 hour. To the reaction mixture thus obtained was added 2N aqueous sodium hydroxide solution, followed by extraction with diethyl ether. The extract was washed with aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The low-boiling fraction was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography. The procedure yielded 4.84 g of 1α,3β-bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-ol (yield: 83%) showing the following physical property.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. customTo the reaction mixture thus obtained
  4. extractionfollowed by extraction with diethyl ether
  5. washThe extract was washed with aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe low-boiling fraction was then distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ae971a8259a2498e92cbfd2fa6d8df24
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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