Sodium Methoxide → 2-Methoxy-2-(trifluoromethyl)-1,3-dioxolane

HRID 483887Notes

Reaction equation

HRID 483887 reaction equation
[CH3:1][O-:2].[Na+].[F:4][C:5]([F:13])([F:12])[C:6]([O:8][CH2:9][CH2:10]Cl)=[O:7]>O1CCCC1>[CH3:1][O:2][C:6]1([C:5]([F:13])([F:12])[F:4])[O:8][CH2:9][CH2:10][O:7]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 125747172-Chloroethyl trifluoroacetate

Product 1

HCID 126652842-Methoxy-2-(trifluoromethyl)-1,3-dioxolaneYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5.4 g (0.10 mol) of sodium methoxide in 50 mL of tetrahydrofuran (THF) was stirred at -20° to -10° while 17.7 g (0.10 mol) of 2-chloroethyl trifluoroacetate were added dropwise. The resulting clear solution was allowed to warm with precipitation commencing at about 10° and a slow exotherm ensuing to 35°. The mixture was maintain below 35° until the exotherm subsided and then was stirred for 4 h. Filtration and fractionation of the filtrate gave 7.4 g (43% yield) of 2-methoxy-2-trifluoromethyl-1,3-dioxolane, b.p. 61°-62° at 3.3 kPa (25 mm). IR (neat): 3000, 2965, 2925, and 2680 (sat'd CH), 1250-1100 cm-1 (CF, C--O). NMR (CCl4): 1H 4.17 (m, 4H, ring CH2 and 3.33 ppm (s, 3H, OCH3); 19F-85.0 ppm (s, CF3).

Workup

  1. additionwere added dropwise
  2. temperatureto warm with precipitation commencing at about 10°
  3. customensuing to 35°
  4. temperatureThe mixture was maintain below 35° until the exotherm
  5. filtrationFiltration and fractionation of the filtrate

Sources & evidence

ORD record
ord-cbe3a8d8c5c24028bd7177a12e0f1e28
Source dataset
uspto-grants-1993_07
Patent number
US05227500

Reaction notes

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