Water → HCID 53434070, compound

HRID 1915542Notes

Reaction equation

HRID 1915542 reaction equation
[CH3:1][O:2][CH:3]([O:19][CH3:20])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:18])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.O>ClCCl.CS(C)=O.C(N(CC)CC)C>[CH3:20][O:19][CH:3]([O:2][CH3:1])[C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:18])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 962WaterHCID 67027749HCID 67027749, compound

Product 1

HCID 53434070HCID 53434070, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

29.16 g (0.183 mol) sulfur trioxide pyridine complex is added in portions to a solution of 33 g 1-[4-(dimethoxymethyl)phenyl]-2-phenylethanol in dichlormethan (540 ml), DMSO (140 ml) and triethylamine (25.5 ml) at 10° C. The mixture is slowly warmed to room temperature and stirred for 2 h. Water is added and the organic phase is separated, washed with 1 mol/l HCl, 3 times with 5% w/w sodium thiosulfate solution and saturated NaCl solution. The combined organic phases are dried over sodium sulfate and the solvens is evaporated. The residue is purified on a silica gel column chromatography (n-Hexan/EtOAc) to yield the desired product.

Workup

  1. customthe organic phase is separated
  2. washwashed with 1 mol/l HCl, 3 times with 5% w/w sodium thiosulfate solution and saturated NaCl solution
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvens is evaporated
  5. customThe residue is purified on a silica gel column chromatography (n-Hexan/EtOAc)

Sources & evidence

ORD record
ord-7e6690d11c1546a79aa0c83ad828fd30
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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