Water → HCID 23113879, compound

HRID 2376372Notes

Reaction equation

HRID 2376372 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:14][O:13][C:12]3[C:15]4[C:20]([C:21]([OH:24])=[C:22]([CH3:23])[C:11]2=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[F:25][C:26]([F:32])([F:31])[S:27]([O-])(=[O:29])=[O:28].O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[F:25][C:26]([F:32])([F:31])[S:27]([O:24][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:12]2[O:13][CH2:14][CH:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)[C:11]=2[C:22]=1[CH3:23])(=[O:29])=[O:28]

Participants

6

Reactant 3

HCID 962WaterHCID 2758875TrifluoromethanesulfonateHCID 23114126HCID 23114126, compound

Product 1

HCID 23113879HCID 23113879, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(4-isopropylphenyl)-4-methyl-2,3-dihydronaphtho[1,2-b]furan-5-ol obtained in Reference Example 252 (2.60 g, 8.17 mmol) and 4-dimethylaminopyridine (2.0 g, 16.3 mmol) in pyridine (30 mL) was added anhydrous trifluoromethanesulfonate (1.51 mL, 9.00 mmol) at room temperature at 0° C., and the mixture was stirred at 50° C. for 8 hours. Water was added to the reaction solution to separate the organic layer, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with 1 N hydrochloric acid and a saturated sodium hydrogen carbonate solution, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to obtain 2.8 g (yield 76%) of the title compound. Oily matter.

Workup

  1. customto separate the organic layer
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with 1 N hydrochloric acid
  4. dry with materiala saturated sodium hydrogen carbonate solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f3285510d9c43dca790a374101f81dc
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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