Hydrochloric Acid → HCID 178455773, compound

HRID 1674432Notes

Reaction equation

HRID 1674432 reaction equation
[CH:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][OH:16])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)=[CH2:2].N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].Cl>CN(C)C1C=CN=CC=1.ClCCl>[CH3:23][S:24]([O:16][CH2:15][C@H:12]1[CH2:13][CH2:14][C@H:9]([C@H:6]2[CH2:7][CH2:8][C@H:3]([CH:1]=[CH2:2])[CH2:4][CH2:5]2)[CH2:10][CH2:11]1)(=[O:26])=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178455769HCID 178455769, compound

Product 1

HCID 178455773HCID 178455773, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

15.1 g of trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethanol, 8.2 mL of pyridine, and 0.41 g of 4-dimethylaminopyridine were dissolved in 50 mL of dichloromethane. A dichloromethane (6 mL) solution containing 6.3 mL of methanesulfonyl chloride was added dropwise to the above solution on ice for 30 minutes. The solution was heated to room temperature, then stirred for 6 hours, and was left over night. The reaction solution was poured into 10% hydrochloric acid, and the organic layer was fractioned. The aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silicagel/toluene) and recrystallization (hexane/toluene) 3 times, to thereby obtain 9.8 g of trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethyl methanesulfonate in the form of colorless crystals.

Workup

  1. additionwas added dropwise to the above solution on ice for 30 minutes
  2. waitwas left over night
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washwashed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (silicagel/toluene) and recrystallization (hexane/toluene) 3 times

Sources & evidence

ORD record
ord-12fef9ec50bc4a999393b33b7a455992
Source dataset
uspto-grants-2011_08
Patent number
US08003006B2

Reaction notes

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