1,3-Propanediol → HCID 54020412, compound

HRID 442977Notes

Reaction equation

HRID 442977 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([O:12][C:13]2[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([CH3:19])[CH:18]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(P(CCCC)CCCC)CCC.[CH2:34](O)[CH2:35][CH2:36][OH:37].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[C:1]([C:3]1[CH:4]=[C:5]([S:9]([O:12][C:13]2[CH:14]=[C:15]([CH:16]=[C:17]([CH3:19])[CH:18]=2)[O:20][CH2:34][CH2:35][CH2:36][OH:37])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

7

Reactant 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 54212462HCID 54212462, compound

Product 1

HCID 54020412HCID 54020412, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 3-(3-cyanophenylsulfonyloxy)-5-methylphenol (2.30 g, 8.0 mmol), as prepared in the preceding step, tri-n-butylphosphine (2.4 g, 12.0 mmol) and 1,3-propanediol (3.0 g, 40 mmol) in anhydrous tetrahydrofuran (50 mL) was added 1,1'-(azodicarbonyl)dipiperidine (3.0 g, 12.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (100 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 (10% ethyl acetate in dichloromethane) to give the title compound as a colorless oil (2.2 g, 79%). 1H-NMR (300 MHz, CDCl3) δ 8.13 (s, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.95 (d, J=7.9 Hz, 1H), 7.71 (t, J=7.9 Hz, 1H), 6.65 (s, 1H), 6.40 (s, 1H), 6.37 (s, 1H), 4.02 (t, J=6.0 Hz, 2H), 3.82 (t, J=6.0 Hz, 2H), 2.26 (s, 3H), 2.00 (t, J=6.0 Hz, 2H), 1.67 (br 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 (10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-af3661cbdbba492e819e6c41542d9dde
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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