Diethyl Ether → HCID 54187349, compound

HRID 1086374Notes

Reaction equation

HRID 1086374 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:2].[NH+:10]1[CH:15]=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:22]([S:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29]O)[CH2:23][CH2:24][CH3:25].[CH2:35]([O:37]CC)[CH3:36]>C(Cl)Cl>[CH2:22]([S:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH:29]=[CH:36][C:35]([N:10]([OH:2])[CH3:15])=[O:37])[CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724130Cornforth reagentHCID 13586448HCID 13586448, compound

Product 1

HCID 54187349HCID 54187349, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium dichromate (284.6 g, .756 mol) is added to 1100 ml of methylene chloride. The compound 2-(n-butylthio)benzyl alcohol (99.0 g, 0.504 mol) in 160 ml of methylene chloride is added and the mixture stirred at room temperature for 2 days. The mixture is poured into 2000 ml of diethyl ether and filtered through diatomeceous earth (Celite®). The solids are washed extensively with diethyl ether and filtered. The filtrate and washings are combined and washed four times with lN HCl and then with brine, and dried over MgSO4 to afford the subtitle compound.

Workup

  1. filtrationfiltered through diatomeceous earth (Celite®)
  2. washThe solids are washed extensively with diethyl ether
  3. filtrationfiltered
  4. washwashed four times with lN HCl
  5. dry with materialwith brine, and dried over MgSO4

Sources & evidence

ORD record
ord-1b348975686f4ba4abefef5dcded5d1b
Source dataset
uspto-grants-1991_07
Patent number
US05028629

Reaction notes

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