Tributylphosphine → HCID 53648570, compound

HRID 1977952Notes

Reaction equation

HRID 1977952 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([O:14][C:15]1[CH:16]=[C:17]([OH:22])[CH:18]=[C:19]([CH3:21])[CH:20]=1)(=[O:13])=[O:12])(=[O:4])=[O:3].[CH3:23]CCCP(CCCC)CCCC.[OH:36][CH2:37][C:38]1(CO)[CH2:40][CH2:39]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[CH3:21][C:19]1[CH:20]=[C:15]([O:14][S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:2]([CH3:1])(=[O:3])=[O:4])(=[O:12])=[O:13])[CH:16]=[C:17]([CH:18]=1)[O:22][CH2:23][CH:37]([CH:38]1[CH2:40][CH2:39]1)[OH:36]

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 41014371,1-Bis(hydroxymethyl)cyclopropaneHCID 17871262HCID 17871262, compound

Product 1

HCID 53648570HCID 53648570, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 3-(2-methylsulfonylphenylsulfonyloxy)-5-methylphenol (6.85 g, 20.0 mmol), as prepared in step a of Example 8, tri-N-butylphosphine (6.1 g, 30 mmol) and 1,1-dihydroxylmethylcyclopropane (5.1 g, 50 mmol), as prepared in the preceding step, in tetrahydrofuran (200 mL) was added 1,1′-(azodicarbonyl)dipiperidine (7.6 g, 30 mmol). The mixture was stirred at room temperature overnight, hexane (300 mL) was added to the mixture and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, the residue was purified by flash column chromatography (1:1 to 2:1 ethyl acetate/hexane) and by crystallization from ethyl acetate/hexane (1:5) to give the title compound as white solid (4.9 g, 57%). 1H-NMR (300 MHz, CDCl3) δ8.45 (d, J=7.8 Hz, 1H), 8.13 (d, J=7.9 Hz, 1H), 7.88 (t, J=7.7 Hz, 1H), 7.75 (t, J=7.7 Hz, 1H), 6.77 (br s, 3H), 3.82 (s, 2H), 3.59 (d, J=5.5 Hz, 2H), 3.45 (s, 3H), 2.23 (s, 3H), 0.61 (s, 4H).

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 to 2:1 ethyl acetate/hexane) and by crystallization from ethyl acetate/hexane (1:5)

Sources & evidence

ORD record
ord-390ecc98390145bc93085c9172ed6a3c
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

Loading…