1,3-Propanediol → HCID 53923924, compound

HRID 442925Notes

Reaction equation

HRID 442925 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)(=[O:12])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.C(P(CCCC)CCCC)CCC.[CH2:33](O)[CH2:34][CH2:35][OH:36].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[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)(=[O:12])=[O:11])[CH:5]=[C:6]([CH:7]=1)[O:8][CH2:33][CH2:34][CH2:35][OH:36]

Participants

7

Reactant 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 10934765HCID 10934765, compound

Product 1

HCID 53923924HCID 53923924, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 5-methyl-3-(3-methylphenylsulfonyloxy)phenol (560 mg, 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 (30 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 colorless oil (605 mg, 90%). 1H-NMR (300 MHz, CDCl3) δ 7.69 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.46 (t, J=7.5 Hz, 1H), 7.41 (t, J=7.6 Hz, 1H), 6.62 (s, 1H), 6.41 (s, 1H), 6.36 (s, 1H), 4.13 (t, J=7.2 Hz, 2H), 3.81 (m, 2H), 2.43 (s, 3H), 2.24 (s, 3H), 1.96 (m, 2H), 1.61 (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 (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2a3c7c1263304452b0793ec56ad9bc42
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

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