Thionyl Chloride → HCID 67302137, compound

HRID 1015378Notes

Reaction equation

HRID 1015378 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=O)[CH2:7][CH2:6]1)([O:3][CH3:4])=[O:2].S(Cl)(Cl)=O.[I-].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Zn+]>O1CCCC1>[CH3:4][O:3][C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([C:11](=[O:13])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[O:20][CH3:19])[CH2:9][CH2:10]1)=[O:2]

Participants

5

Reactant 3

HCID 24386Thionyl Chloride2×HCID 178489637HCID 178489637, compoundHCID 178501163HCID 178501163, compound

Product 1

HCID 67302137HCID 67302137, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an oven dried 1 neck round bottom flask with reflux condenser and stirbar, trans-4-carbomethoxycyclohexane-1-carboxylic acid (1.11 g; 5.4 mmol) was heated to reflux in the presence of 30 mL thionyl chloride. After 3 hours reflux, mixture cooled to 40° C. under nitrogen flow, and excess thionyl chloride was removed at reduced pressure. Residue was taken up in 5 mL of dry tetrahydrofuran and added to a 0° C. mixture of 2-methoxyphenylzinc iodide (11.0 mL; 5.4 mmol), tetrakis(triphenylphospine)palladium (0) (90 mg; 0.08 mmol) in 2.5 mL anhydrous tetrahydrofuran. Mixture was allowed to warm to room temperature over 16 hours. Reaction was quenched with 6 mL 1N HCl and ethyl acetate was taken in. Organics separated and aqueous re-extracted with 20 mL ethyl acetate. Combined organics were washed with sat. NaHCO3, water, brine and dried over MgSO4. Material was purified via flash silica plug (10:1) using 15% ethyl acetate in hexanes isocratic to give 900 mg of title compound. (64% yield)

Workup

  1. customIn an oven dried 1 neck round bottom flask
  2. temperaturewith reflux condenser
  3. temperatureAfter 3 hours reflux
  4. customwas removed at reduced pressure
  5. additionadded to a 0° C.
  6. customReaction
  7. customwas quenched with 6 mL 1N HCl and ethyl acetate
  8. customOrganics separated
  9. extractionaqueous re-extracted with 20 mL ethyl acetate
  10. washCombined organics were washed with sat. NaHCO3, water, brine
  11. dry with materialdried over MgSO4
  12. customMaterial was purified via flash silica plug (10:1)

Sources & evidence

ORD record
ord-a639322cce4d4f188ef9bc27c58d0a94
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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