Hydrochloric Acid → HCID 15279122, compound

HRID 1609147Notes

Reaction equation

HRID 1609147 reaction equation
O1CCCC1.Cl.[C:7]([C:9]1([O:16][Si](C)(C)C)[CH2:14][CH:13]2[CH2:15][CH:10]1[CH2:11][CH2:12]2)#[N:8].C(=O)([O-])O.[K+]>O>[C:7]([C:9]1([OH:16])[CH2:14][CH:13]2[CH2:15][CH:10]1[CH2:11][CH2:12]2)#[N:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516893Potassium BicarbonateHCID 12812046HCID 12812046, compound

Product 1

HCID 15279122HCID 15279122, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a 200 milliliter Erlenmeyer flask, 38.37 grams (183.3 millimoles) of 2-cyano-2-trimethylsiloxynorbornane obtained in A, a PTFE-coated stirrer bar, 30 milliliters of tetrahydrofuran, 10 milliliters of water, and 1 milliliter of 2N hydrochloric acid were placed. This mixture was vigorously stirred at room temperature. Three hours later, the disappearance of the starting norbornane compound was confirmed by thin-layer chromatography, and 1 milliliter of 2N aqueous potassium hydrogencarbonate solution was then added to the reaction mixture and the mixture was vigorously stirred for 5 minutes. The reaction mixture was poured into water and extracted three times with diethyl ether, and the extracts were combined, washed with brine, and dried with anhydrous sodium sulfate. The sodium sulfate was then filtered out. The solvent was subsequently removed in vacuo to thereby yield a crude product. Distillation of the crude product under reduced pressure gave 2-cyano-2-hydroxynorbornane (exo/endo mixture) as a colorless, clear liquid having a boiling point of 85.5°-86.0° C. (0.35 mmHg).

Workup

  1. customThree hours
  2. additionwas then added to the reaction mixture
  3. stirringthe mixture was vigorously stirred for 5 minutes
  4. extractionextracted three times with diethyl ether
  5. washwashed with brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. filtrationThe sodium sulfate was then filtered out
  8. customThe solvent was subsequently removed in vacuo
  9. customto thereby yield a crude product
  10. distillationDistillation of the crude product under reduced pressure

Sources & evidence

ORD record
ord-d7f45c4c99714e18a58215f736a24390
Source dataset
uspto-grants-1995_03
Patent number
US05399647

Reaction notes

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