Methanol, trifluoro- → HCID 89646167, compound

HRID 1423380Notes

Reaction equation

HRID 1423380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[CH2:22][CH2:23][CH:24]([OH:29])[C:25]([F:28])([F:27])[F:26])[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.FC(O)(F)F>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[CH2:22][CH2:23][C:24](=[O:29])[C:25]([F:26])([F:27])[F:28])[CH2:13]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73894Methanol, trifluoro-HCID 159087TriacetoxyperiodinaneHCID 56639596HCID 56639596, compound

Product 1

HCID 89646167HCID 89646167, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Chloro-N-((R/S)-5-((R/S)-4,4,4-trifluoro-3-hydroxybutyl)-1,2,3,4-tetrahydronaphthalen-2-yl)benzenesulfonamide, designated as (+/−)-22/(+/−)-22 in FIG. 10, was prepared as follows. Dess-Martin periodinane (128.8 mg, 0.30 mmol) was added to a solution of the trifluoromethyl alcohol (67.6 mg, 0.15 mmol) in dichloromethane (4 mL) and the reaction was stirred at room temperature for 2 hour. The reaction mixture was diluted with dichloromethane and washed with water. The organic layer was separated, dried over magnesium sulfate and concentrated to dryness. Silica gel chromatography (20% ethyl acetate in hexanes), gave the purified product, (R/S)-4-chloro-N-(5-(4,4,4-trifluoro-3-oxobutyl)-1,2,3,4-tetrahydronaphthalen-2-yl)benzenesulfonamide, as colorless oil (51.1 mg). Yield 76%.

Workup

  1. customwas prepared
  2. washwashed with water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ddae4855125f438cade39643d16cd194
Source dataset
uspto-grants-2015_01
Patent number
US08927586B2

Reaction notes

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