Water → HCID 10914827, compound

HRID 1700954Notes

Reaction equation

HRID 1700954 reaction equation
[I-:1].[Na+].CS(O[CH2:8][CH2:9][CH2:10][C@H:11]([CH3:21])[CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])(=O)=O.O>CC(C)=O.[Cl-].[Na+].O>[I:1][CH2:8][CH2:9][CH2:10][C@H:11]([CH3:21])[CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 10881469HCID 10881469, compound

Product 1

HCID 10914827HCID 10914827, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

Anhydrous sodium iodide (600 mg, 4.0 mmol, 2 equiv) is added to a solution of (S)-1-methanesulfonyloxy-5-(tert-butyldimethylsilyloxy)-4-methyl-pentane 7 (622 mg, 2.0 mmol) in 3.0 ml of absolute acetone. The mixture is stirred for 2 h at 50° C. 10 ml of a mixture of brine and water (1:1) are added, and the mixture is extracted with diethyl ether (3×20 ml). The combined organic extracts are dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by flash column chromatography (pentane/diethyl ether 20:1) affords (S)-1-iodo-5-(tert-butyidimethylsilyloxy)-4-methyl-pentane 8 (647 mg, 94%) as a colourless oil. FG 342.34; 13C-NMR (100 MHz, CDCl3): δ=68.1, 35.1, 34.3, 31.3, 26.0, 16.7, 7.4, −5.3

Workup

  1. extractionthe mixture is extracted with diethyl ether (3×20 ml)
  2. dry with materialThe combined organic extracts are dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash column chromatography (pentane/diethyl ether 20:1)

Sources & evidence

ORD record
ord-64354fc865844d1f9cc31b9704dfce5c
Source dataset
uspto-grants-2002_02
Patent number
US06350878B1

Reaction notes

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