Ethylene Glycol → HCID 178502716, compound

HRID 579588Notes

Reaction equation

HRID 579588 reaction equation
[CH3:1][O:2][N:3]([CH3:21])[C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5].[CH2:22]([O:24]C(OCC)OCC)[CH3:23].C(O)CO>C1(C)C=CC=CC=1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>[CH3:1][O:2][N:3]([CH3:21])[C:4]([C@H:6]1[CH2:7][CH2:8][C@@H:9]([C:12]2([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[O:24][CH2:22][CH2:23][O:20]2)[CH2:10][CH2:11]1)=[O:5]

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 31214Ethyl orthoformateHCID 178502722HCID 178502722, compound

Product 1

HCID 178502716HCID 178502716, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 124969952-Methylbenzenesulfonic acid hydrateCatalystHCID 1140TolueneSolvent

Procedure

A solution of cis-4-(4-chlorobenzoyl)-cyclohexanecarboxylic acid, methoxy-methyl amide (1.6 g, 5.17 mmol), triethylorthoformate (843 mg, 0.95 mL, 5.7 mmol), ethylene glycol (1.6 g, 1.45 mL, 25.9 mmol) and toluenesulfonic acid monohydrate (50 mg) in toluene (50 mL) was stirred overnight at 60° C., and then cooled to room temperature and concentrated to dryness in vacuo. The reaction mixture was redissolved in ethyl acetate, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Purification by flash column chromatography (silica gel, 0-30% ethyl acetate in heptane) gave cis-4-[2-(4-chlorophenyl)-[1,3]-dioxolan-2-yl]-cyclohexanecarboxylic acid, methoxy-methyl amide as a colorless oil (1.36 g, 74%); 1H NMR (CDCl3, 300 MHz) δ 7.33 (d, J=8.5 Hz,), 7.27 (d, J=8.5 Hz, 2H), 3.96 (m, 2H), 3.68 (m, 2H), 3.64 (s, 3H), 3.14 (s, 3H), 2.83 (m, 1H), 1.96 (m, 2H), 1.76 (m, 1H), 1.67 (m, 3H) and 1.47 (m, 4H); MS (+CI): m/z for C18H24ClNO4: expected 353.1. found 354.2 (M+H)+.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. dissolutionThe reaction mixture was redissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography (silica gel, 0-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-09b0f12e01aa4af08a2afa56367ba71f
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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