Methyl iodide → HCID 57434729, compound

HRID 1863975Notes

Reaction equation

HRID 1863975 reaction equation
[H-].[Na+].[CH3:3][C@H:4]([CH2:7][O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])[CH2:5][OH:6].CI.[CH3:21]COC(C)=O.CCCCCCC>CN(C)C=O.COC(C)(C)C>[CH:13]([Si:9]([CH:10]([CH3:11])[CH3:12])([CH:16]([CH3:18])[CH3:17])[O:8][CH2:7][C@@H:4]([CH3:3])[CH2:5][O:6][CH3:21])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10705611HCID 10705611, compoundHCID 21899848Ethylacetate heptane

Product 1

HCID 57434729HCID 57434729, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

3.09 g of sodium hydride (60% dispersion in oil) are added to a solution of 9.55 g of (S)-2-methyl-3-triisopropylsilanyloxypropan-1-ol [256643-28-4] and 7.3 ml of methyl iodide in 70 ml of N,N-dimethylformamide at 0° C. After 60 hours at room temperature, the reaction mixture is diluted with tert-butyl methyl ether and washed successively with water and brine, dried with sodium sulfate and evaporated. The residue is purified by flash chromatography (SiO2 60F) to afford the title as a yellow oil. Rf=0.51 (EtOAc-heptane 1:10).

Workup

  1. washwashed successively with water and brine
  2. dry with materialdried with sodium sulfate
  3. customevaporated
  4. customThe residue is purified by flash chromatography (SiO2 60F)
  5. customto afford the title as a yellow oil

Sources & evidence

ORD record
ord-bede5fcec1444e47886c375230ebf755
Source dataset
uspto-grants-2009_12
Patent number
US07625893B2

Reaction notes

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