Triethylamine → HCID 118271620, compound

HRID 595187Notes

Reaction equation

HRID 595187 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][CH3:16])=[O:14])[C:9]([CH3:18])([CH3:17])[CH2:8]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:17][C:9]1([CH3:18])[CH2:8][CH:7]([O:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:12][CH2:11][CH:10]1[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 118998220HCID 118998220, compound

Product 1

HCID 118271620HCID 118271620, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (1.69 mL, 21.7 mmol) was added at −20° C. to a solution of racemic methyl 4-hydroxy-2,2-dimethylcyclohexanecarboxylate (3.11 g, 16.7 mmol) and triethylamine (4.65 mL, 33.4 mmol) in dichloromethane (67 mL). The reaction was stirred for 3 hours. Saturated aqueous sodium bicarbonate was added to the mixture and extracted with dichloromethane (3×). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford methyl 2,2-dimethyl-4-[(methylsulfonyl)oxy]cyclohexanecarboxylate. 1H NMR (500 MHz, CDCl3) δ 4.92-4.72 (m, 1H), 3.64 (s, 3H), 2.99 (s, 3H), 2.29-2.15 (m, 1H), 2.15-2.00 (m, 1H), 1.99-1.87 (m, 1H), 1.83-1.71 (m, 2H), 1.63-1.59 (m, 1H), 1.49-1.32 (m, 1H), 1.01 (s, 6H).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d81267f076bc428ca9ce1a26ea8cd743
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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