Triethylamine → HCID 118271620, compound

HRID 595209Notes

Reaction equation

HRID 595209 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[OH:13][CH:14]1[CH2:19][CH2:18][CH:17]([C:20]([O:22][CH3:23])=[O:21])[C:16]([CH3:25])([CH3:24])[CH2:15]1>ClCCl.O>[CH3:24][C:16]1([CH3:25])[CH2:15][CH:14]([O:13][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:19][CH2:18][CH:17]1[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118998220HCID 118998220, compound

Product 1

HCID 118271620HCID 118271620, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (2.6 g, 22 mmol) and triethylamine (2.4 g, 22 mmol) were added to a solution of methyl 4-hydroxy-2,2-dimethylcyclohexanecarboxylate (1.38 g, 7.4 mmol) in dichloromethane (30 mL) at 0° C. The mixture was stirred at room temperature for 16 hours. Then the mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether) to give methyl 2,2-dimethyl-4-[(methylsulfonyl)oxy]cyclohexanecarboxylate. 1H NMR (400 MHz, CDCl3): δ 5.30-4.78 (m, 1H), 3.65 (s, 3H), 3.05 (s, 3H), 2.25-2.21 (m, 1H), 2.19-2.13 (m, 2H), 1.90-1.88 (m, 1H), 1.79-1.75 (m, 2H), 1.63 (s, 1H), 1.06 (s, 6H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-5ff68b140981404ca0a25c0a10fbdf40
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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