Formic Acid → HCID 178466567, compound

HRID 1793274Notes

Reaction equation

HRID 1793274 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH:20]2OCCC[O:21]2)[CH2:14][CH2:13]1.C(O)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C@H:12]1[CH2:17][CH2:16][C@H:15]([CH2:18][CH2:19][CH:20]=[O:21])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 178466566HCID 178466566, compound

Product 1

HCID 178466567HCID 178466567, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 2-(2-(trans-4-(2,3-difluoro-4-ethoxyphenyl)-cyclohexyl)-ethyl)-1,3-dioxane (19.8 mmol) obtained by the reaction of Step 4 was dissolved in 100 ml of toluene, 87% formic acid (198 mmol) was added, and the solution was heated to reflux for 4 hours. The reaction solution was twice washed with 50 ml of a saturated aqueous solution of sodium hydrogen carbonate, then three times with 50 ml of water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, to form crude 3-(trans-4-(2,3-difluoro-4-ethoxyphenyl)-cyclohexyl)-propanal (19.8 mmol).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 4 hours
  3. washThe reaction solution was twice washed with 50 ml of a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialthree times with 50 ml of water, and dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c5d2a3c98a094bf9b2875bcfff8c573c
Source dataset
uspto-grants-2006_07
Patent number
US07081279B2

Reaction notes

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