Water → HCID 13844179, compound

HRID 974685Notes

Reaction equation

HRID 974685 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[H-].[Na+].[CH3:12][O:13][CH2:14][CH2:15][O:16][CH2:17]Cl.O>O1CCCC1>[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][O:8][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 7528SolketalHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethane

Product 1

HCID 13844179HCID 13844179, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

7(a) A solution of 9.25 g of (4RS)-2,2-dimethyl 1.3-dioxolane-4-methanol in 100 ml of tetrahydrofuran was added dropwise to a suspension of 3.36 g of sodium hydride (as a 55% w/w dispersion in mineral oil) in 300 ml of tetrahydrofuran at 20° to 24° C. over a period of 30 minutes. At the end of this time. 10.46 g of 2-methoxyethoxymethyl chloride in 50 ml of tetrahydrofuran were added dropwise to the mixture cooled on an ice bath. The reaction mixture was stirred at 0° to 2° C. for 3 hours, and then poured into water. It was then extracted twice with ethyl acetate. The combined extracts were washed with water, dried and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 200 g of silica gel. 12.80 g of (4RS)-2,2-dimethyl-4-(2-methoxyethoxy)methoxymethyl-1,3-dioxolane were obtained as a colorless oil from the fractions eluted with mixtures of ethyl acetate and hexane ranging from 1:5 to 1:4 by volume.

Workup

  1. temperaturecooled on an ice bath
  2. extractionIt was then extracted twice with ethyl acetate
  3. washThe combined extracts were washed with water
  4. customdried
  5. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3951f05e72e14d5098126bf779feecbc
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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