Potassium Carbonate → N-(4-[2-(3,4-di(methoxymethoxy)phenyl)-trans-vinyl]benzenesulfonyl}morpholine

HRID 1866461Notes

Reaction equation

HRID 1866461 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Li+].[Cl-].[CH3:25][O:26][CH2:27][O:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=1[O:37][CH2:38][O:39][CH3:40])[CH:32]=[CH2:33]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH3:25][O:26][CH2:27][O:28][C:29]1[CH:30]=[C:31](/[CH:32]=[CH:33]/[C:2]2[CH:7]=[CH:6][C:5]([S:8]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)[CH:34]=[CH:35][C:36]=1[O:37][CH2:38][O:39][CH3:40]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 2531284-[(4-Bromobenzene)sulfonyl]morpholineHCID 433294Lithium ChlorideHCID 574309473,4-Di(methoxymethoxy)styrene

Product 1

HCID 68977146N-(4-[2-(3,4-di(methoxymethoxy)phenyl)-trans-vinyl]benzenesulfonyl}morpholineYield 83.1%

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

N-(4 -bromobenzenesulfonyl)morpholine (1.0 g, 3.266 mmol) was mixed with (n-Bu)4NBr (TBAB, 1.05 g, 3.266 mmol), K2CO3 (0.451 g, 3.266 mmol) and LiCl (0.1384 g, 3.266 mmol under argon atmosphere. Then dry DMF (25 mL) and 3,4-di(methoxymethoxy)styrene (0.7324 g, 3.226 mmol) were added, followed by the catalyst Pd(OAc)2 (73 mg, 0.3266 mmol). The mixture was heated between 80-90° C. under argon atmosphere for 24 hours. After removal of the DMF solvent, the residue obtained was loaded to a silica gel column with CH2Cl2 as solvent. The column was eluted with CH2Cl2/EtOAc (2:1, v/v) to yield 1.205 g of N-{4-[2-(3,4-di(methoxymethoxy)phenyl)-trans-vinyl]benzenesulfonyl}morpholine as a yellowish solid (2.6805 mmol, yield 82.1%). 1H NMR (CDCl3, 300.16 MHz) δ (ppm) 7.72 (d, J=8.5 Hz, 2H), 7.64 (d, J=8.5 Hz, 2H), 7.38 (d, J=1.7 Hz, 1H), 7.20-7.13 (m, 3H), 7.00 (d, J=16.2 Hz, 1H), 5.30 (s, 2H), 5.27 (s, 2H), 3.77-3.74 (m, 4H), 3.56 (s, 3H), 3.53 (s, 3H) and 3.04-3.01 (m, 4H). MS (ESI) m/z: 450 (M+1)+ and 472 (M+23)+.

Workup

  1. customAfter removal of the DMF solvent
  2. customthe residue obtained
  3. washThe column was eluted with CH2Cl2/EtOAc (2:1

Sources & evidence

ORD record
ord-2c6a5710c3e541ca89d6366b3eec7d84
Source dataset
uspto-grants-2009_12
Patent number
US07629375B2

Reaction notes

Loading…