1,3-Propanediol → 3-[5-Methyl-3-(1-naphthalenylsulfonyloxy)phenoxy]propanol

HRID 442956Notes

Reaction equation

HRID 442956 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][S:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.C(P(CCCC)CCCC)CCC.[CH2:36](O)[CH2:37][CH2:38][OH:39].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]([O:9][S:10]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:5]=[C:6]([CH:7]=1)[O:8][CH2:36][CH2:37][CH2:38][OH:39]

Participants

7

Reactant 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 539777205-Methyl-3-(1-naphthalenylsulfonyloxy)phenol

Product 1

HCID 542805743-[5-Methyl-3-(1-naphthalenylsulfonyloxy)phenoxy]propanolYield 87.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 5-methyl-3-(1-naphthalenylsulfonyloxy)phenol (620 g, 2.0 mmol), as prepared in the preceding step, tri-n-butylphosphine (607 mg, 3.0 mmol) and 1,3-propanediol (760 mg, 10 mmol) in anhydrous tetrahydrofuran (20 mL) was added 1,1'-(azodicarbonyl)dipiperidine (757 mg, 3.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (50 mL) was added to the mixture, and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (1:1 hexane/ethyl acetate) to give the title compound as a yellow oil (650 mg, 87%). 1H-NMR (300 MHz, CDCl3) δ 8.80 (d, J=8.6 Hz, 1H), 8.14 (d, J=7.3 Hz, 2H), 7.98 (d, J=8.2 Hz, 1H), 7.78 (t, J=8.5 Hz, 1H), 7.67 (t, J=8.1 Hz, 1H), 7.49 (t, J=8.1 Hz, 1H), 6.54 (s, 1H), 6.33 (s, 1H), 6.22 (s, 1H), 3.84 (t, J=6.0 Hz, 2H), 3.75 (t, J=6.0 Hz, 2H), 2.15 (s, 3H), 1.90 (m, 2H), 1.59 (s, 1H).

Workup

  1. customthe precipitates were removed by filtration
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2e818bced2cc414881109500370f5c8d
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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