Tetrahydrofuran → HCID 53677278, compound

HRID 982408Notes

Reaction equation

HRID 982408 reaction equation
[C:1]1([CH:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH2:8]CO)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].[O:34]1[CH2:38]CCC1>>[CH3:38][O:34][S:30]([CH2:29][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=1)(=[O:32])=[O:31]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15132273HCID 15132273, compound

Product 1

HCID 53677278HCID 53677278, compound

Conditions

Temperature
0 °C

Procedure

3-Phenyl-4-(4-trifluoromethylphenyl)butanol (3.65 g, 12.4 mmole) was dissolved in 50 ml of tetrahydrofuran and the resulting solution was cooled to about 0° C. Triethylamine (1.82 ml, 13.0 mmole) was added, followed by the dropwise addition of 1.01 ml (13.0 mmole) of methanesulfonyl chloride over a five minute period. The solution was stirred at room temperature (22° C.) for about 2 hours. The reaction solution was then partitioned between ethyl acetate and water. The resulting organic layer was washed with a saturated brine solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to provide 4.47 g of 3-phenyl-4-(4-trifluoromethylphenyl)butane sulfonic acid methyl ester as a yellow oil. N.M.R. analysis (300 MHz instrument, in CDCl3) provided: δ=1.98-2.25 (broad multiplet, 2H); 2.80 (singlet, 3H); 3.00 (multiplet, 3H); 3.92 and 4.09 (multiplet, 2H); 7.02-7.45 (multiplet, 9H).

Workup

  1. customThe reaction solution was then partitioned between ethyl acetate and water
  2. washThe resulting organic layer was washed with a saturated brine solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45ad6ff1eb4d4788bd1f2848bc84efea
Source dataset
uspto-grants-1991_02
Patent number
US04996235

Reaction notes

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