Water → Hexamethyldisiloxane

HRID 1706040

Reaction equation

HRID 1706040 reaction equation
[CH3:1][C@@H:2]([C@@H:10]1[C@@:14]2([CH3:29])[CH2:15][CH2:16][CH2:17]/[C:18](=[CH:19]\[CH:20]=[C:21]3\[CH2:22][C@@H:23]([OH:28])[CH2:24][CH2:25][C:26]\3=[CH2:27])/[C@@H:13]2[CH2:12][CH2:11]1)[CH2:3][CH2:4][CH2:5][C:6]([OH:9])([CH3:8])[CH3:7].C(Cl)(=O)C1C=CC=CC=1.[CH3:39][Si:40]([CH3:43])([CH3:42])Cl.[OH2:44]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:1][C@@H:2]([C@@H:10]1[C@@:14]2([CH3:29])[CH2:15][CH2:16][CH2:17]/[C:18](=[CH:19]\[CH:20]=[C:21]3\[CH2:22][C@@H:23]([OH:28])[CH2:24][CH2:25][C:26]\3=[CH2:27])/[C@@H:13]2[CH2:12][CH2:11]1)[CH2:3][CH2:4][CH2:5][C:6]([OH:9])([CH3:7])[CH3:8].[CH3:39][Si:40]([O:44][Si:40]([CH3:43])([CH3:42])[CH3:39])([CH3:43])[CH3:42]

Participants

8

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 7412Benzoyl chlorideHCID 528373125-Hydroxyvitamin D3

Product 2

HCID 24764HexamethyldisiloxaneHCID 528373125-Hydroxyvitamin D3

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 25-hydroxycholecalciferol (5.0 g.) in pyridine (25 ml.) at -15°, under an atmosphere of argon, is added 4-(N,N-dimethylamino)-pyridine (50 mg) followed by benzoyl chloride (2.10 ml.). The solution is warmed to 0° and kept at this temperature for 1.5 hours. After cooling to -15°, trimethylchlorosilane (1.75 ml.) is added and then the mixture is heated to room temperature for 10 minutes, before pouring into water. The mixture is extracted with hexane (500 ml.) and the extracts washed with brine, dilute hydrochloric acid, brine, sodium bicarbonate solution, brine and then dried over sodium sulfate. Evaporation of the solution yields 25-hydroxycholecalciferol, 3-benzoate, trimethylsilylether as an oil.

Workup

  1. temperatureThe solution is warmed to 0°
  2. temperatureAfter cooling to -15°
  3. extractionThe mixture is extracted with hexane (500 ml.)
  4. washthe extracts washed with brine, dilute hydrochloric acid, brine, sodium bicarbonate solution, brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solution

Sources & evidence

ORD record
ord-bd3e980da6fa4280906293410f0432c2
Source dataset
uspto-grants-1980_06
Patent number
US04206131

Linked notes

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