Tetrahydrofuran → 3-[3-(5-Chloro-1,3-dimethylpyrazole-4-sulfonyloxy)-5-methylphenoxy]propanol

HRID 442942Notes

Reaction equation

HRID 442942 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)(=[O:11])=[O:10].[O:21]1C[CH2:24][CH2:23][CH2:22]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(O)CCO.C(P(CCCC)CCCC)CCC>C(OCC)C>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:20][CH2:24][CH2:23][CH2:22][OH:21])(=[O:10])=[O:11]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 545259863-(5-Chloro-1,3-Dimethylpyrazole-4-sulfonyloxy)-5-methylphenol

Product 1

HCID 540486313-[3-(5-Chloro-1,3-dimethylpyrazole-4-sulfonyloxy)-5-methylphenoxy]propanolYield 64%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 318 mg (0.951 mmol) of 3-(5-chloro-1,3-dimethyl-pyrazole-4-sulfonyloxy)-5-methylphenol, as prepared in the preceding step, in 5 mL of anhydrous tetrahydrofuran containing 360 mg (1.42 mmol) of 1,1'-(azodicarbonyl)dipiperidine and 150 μL (2.07 mmol) of 1,3-propanediol was added slowly 350 μL (1.41 mmol) of tri-n-butylphosphine. The reaction mixture was stirred for 1 h at ambient temperature, diluted with diethyl ether, and filtered. The filtrate was concentrated and purified by flash chromatography (ethyl acetate/dichloromethane (2:1)) to give 227 mg (64% yield) of the title compound as an oil. 1H-NMR (300 MHz, CDCl3) δ 6.64-6.65 (m, 1H), 6.52-6.54 (m, 1H), 6.46-6.47 (t, 1H), 4.06 (t, 2H, J=6 Hz), 3.83 (t, 2H, J=6 Hz), 3.82 (s, 3H), 2.29 (s, 3H), 2.28 (s, 3H), 2.00 (pentet, 2H, J=6 Hz). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C15H19ClN2O5S: 375.1 (M+H), 397.1 (M+Na). Found: 374.9, 397.1.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by flash chromatography (ethyl acetate/dichloromethane (2:1))

Sources & evidence

ORD record
ord-1e2fba1d0d694b9ebb37a02165790aa4
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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