Methyl iodide → HCID 22855814, compound

HRID 1757696Notes

Reaction equation

HRID 1757696 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([CH3:37])[CH2:10][C@H:11]([OH:36])[C@@H:12]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@H:13]([O:26][CH3:27])[CH2:14][C@@H:15]([CH3:25])[CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[H-].[Na+].[CH3:40]I>O1CCCC1>[C:1]([O:7][CH2:8][C@H:9]([CH3:37])[CH2:10][C@H:11]([O:36][CH3:40])[C@@H:12]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C@@H:13]([O:26][CH3:27])[CH2:14][C@@H:15]([CH3:25])[CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:22])[CH3:23])([CH3:19])[CH3:20])(=[O:6])[C:2]([CH3:3])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22855818HCID 22855818, compound

Product 1

HCID 22855814HCID 22855814, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Pivaloate 22 (3.52 g, 6.50 mmol) was dissolved in 50 ml of tetrahydrofuran at 25° C. and 523 mg of NaH (60% dispersion in mineral oil) and 4.0ml of anhydrous methyl iodide (10 equiv) were added successively. The solution was stirred at 25° C. for 24 hr. The mixture was partitioned between 150 ml of diethyl ether and 50 ml of water. The aqueous phase was extracted with an additional 2×100 ml of ether. The organic phases were combined, washed with 100 ml of saturated sodium chloride solution and dried over magnesium sulfate. Concentration in vacuogave 3.82 g of 23 as a crude oil. The material was purified by column chromatography on 190 g of silica gel eluting with hexanes:ethyl acetate (8:1) to give 3.58 g (99%) of dimethoxy pivaloate 23. This material was homogeneous by 1H and 13C NMR.

Workup

  1. customThe mixture was partitioned between 150 ml of diethyl ether and 50 ml of water
  2. extractionThe aqueous phase was extracted with an additional 2×100 ml of ether
  3. washwashed with 100 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentration in vacuogave 3.82 g of 23 as a crude oil
  6. customThe material was purified by column chromatography on 190 g of silica gel eluting with hexanes:ethyl acetate (8:1)

Sources & evidence

ORD record
ord-1a3c695f6543481da366ba973fb42a23
Source dataset
uspto-grants-1995_08
Patent number
US05446158

Reaction notes

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