Triethylamine → HCID 86613264, compound

HRID 75192Notes

Reaction equation

HRID 75192 reaction equation
[CH:1]([O:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)=[CH2:2].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:13][S:14]([O:12][CH2:11][CH:8]1[CH2:9][CH2:10][CH:5]([CH2:4][O:3][CH:1]=[CH2:2])[CH2:6][CH2:7]1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 163934Cyclohexanemethanol, 4-[(ethenyloxy)methyl]-

Product 1

HCID 86613264HCID 86613264, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

4-[(Vinyloxy)methyl]cyclohexylmethanol (2.0 g, 0.010 mol) was dissolved in chloroform (20 mL), cooled to 0° C., and then methanesulfonyl chloride (0.85 mL, 0.011 mol) and triethylamine (1.5 mL, 0.011 mol) were added. The reaction was stirred at 0° C. for 2 hours. The reaction was extracted with ethyl acetate, and the extracts were washed with water, brine, and then dried over MgSO4 and concentrated. The product was purified via column chromatography on silica gel (40% ethyl acetate, 60% hexanes), to give 1.53 g of the desired product as a 3:1 mixture of the two diastereomers. 1H NMR (400 MHz, CDCl3): δ 6.36-6.41 (m, 1H), 4.04-4.10 (m, 2H), 3.94-3.96 (m, 2H), 3.39-3.43 (m, 2H), 2.92 (s, 3H), 0.90-1.80 (m, 10 H) (major diastereomer).

Workup

  1. extractionThe reaction was extracted with ethyl acetate
  2. washthe extracts were washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified via column chromatography on silica gel (40% ethyl acetate, 60% hexanes)

Sources & evidence

ORD record
ord-eef175220de240c88719c5a2866fba24
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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