Dimethylformamide → HCID 70380161, compound

HRID 1194998Notes

Reaction equation

HRID 1194998 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]/[CH:10]=[CH:11]\[CH:12]([OH:14])[CH3:13])=[CH:5][CH:4]=1.C(Cl)Cl.CN(C)C=O.[C:23]([Si:27]([CH3:30])([CH3:29])Cl)([CH3:26])([CH3:25])[CH3:24]>CCOCC.C(N(CC)CC)C>[Si:27]([O:14][CH:12]([CH3:13])/[CH:11]=[CH:10]\[S:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 70380177HCID 70380177, compound

Product 1

HCID 70380161HCID 70380161, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

14.1 g (67.1 mmol) of rac-(Z)-4-[(p-methoxyphenyl)thio]-3-buten-2-ol in 250 ml of of methylene chloride and 25 ml of N,N-dimethylformamide are treated with 15.2 g (100 mmol) of t-butyldimethylchlorosilane and 13.6 g (18.7 ml) of triethylamine, the reaction mixture is stirred at room temperature for 6 hours and evaporated. The oil obtained is taken up in 500 ml of ether, washed three times with 100 ml of water each time, dried over sodium sulphate and filtered through silica gel. There is obtained 4-[[(Z)-3-(t-butyldimethylsilyloxy)-1-butenyl]thio]anisole.

Workup

  1. customevaporated
  2. customThe oil obtained
  3. washwashed three times with 100 ml of water each time
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered through silica gel

Sources & evidence

ORD record
ord-967081c8e8b3403c8d25f120f3966923
Source dataset
uspto-grants-1989_03
Patent number
US04816581

Reaction notes

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