Methyl iodide → HCID 15570875, compound

HRID 1772331Notes

Reaction equation

HRID 1772331 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][C@@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].I[CH3:13]>C1COCC1.C(OCC)C>[CH3:13][O:8][CH2:7][C@H:5]1[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 736057(+)-Solketal

Product 1

HCID 15570875HCID 15570875, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol (9.8 g, 74.2 mmol) in anhydrous THF (150 mL) at 0° C. was added sodium hydride (60% in mineral oil) (3.26 g, 82 mmol) in 4 portions over 5 min (caution: gas evolution). The reaction was stirred for an additional 15 min at 0° C., then iodomethane (5.09 mL, 82 mmol) was added and the reaction was warmed to rt. After approximately 1 h at rt, the reaction was diluted with diethyl ether (100 mL), filtered and concentrated to 15-20 mL under vacuum. The yellow liquid was used in the next step without purification.

Workup

  1. temperaturethe reaction was warmed to rt
  2. waitAfter approximately 1 h at rt
  3. filtrationfiltered
  4. concentrationconcentrated to 15-20 mL under vacuum
  5. customThe yellow liquid was used in the next step without purification

Sources & evidence

ORD record
ord-457b874493c442b0915dcf7164f4580e
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

Loading…