Trimethyl orthoformate → (2,2-Bis(fluoromethyl)-1,3-dioxan-5-yl)methanol

HRID 1645535Notes

Reaction equation

HRID 1645535 reaction equation
[OH:1][CH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[F:8][CH2:9][C:10]([CH2:12][F:13])=O.C(OC)(OC)OC.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(N(CC)CC)C>[F:8][CH2:9][C:10]1([CH2:12][F:13])[O:5][CH2:4][CH:3]([CH2:6][OH:7])[CH2:2][O:1]1

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 78432TrimethylolmethaneHCID 2283971,3-DifluoroacetoneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 59792580(2,2-Bis(fluoromethyl)-1,3-dioxan-5-yl)methanolYield 43.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(hydroxymethyl)-1,3-propanediol (2.2 g, 20.7 mmol), 1,3-difluoroacetone (3.89 g, 41.4 mmol), trimethyl orthoformate (3.44 ml, 20.7 mmol), and p-toluenesulfonic acid monohydrate (356 mg, 2.07 mmol) was stirred at 60° C. for 10 hours. After completion of the reaction, triethylamine (577 μl) was added to the reaction mixture, which was then concentrated. The residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate) to obtain the title compound (1.6 g, yield: 43.4%) as a light yellow oil.

Workup

  1. additionwas added to the reaction mixture, which
  2. concentrationwas then concentrated
  3. customThe residue was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate)

Sources & evidence

ORD record
ord-606aab84a7fb407cb6cce2c5777e738e
Source dataset
uspto-grants-2012_02
Patent number
US08124780B2

Reaction notes

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