Ethyl vinyl ether → HCID 15934455, compound

HRID 486304Notes

Reaction equation

HRID 486304 reaction equation
[C:1]1([CH:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]([OH:11])[CH:9]=[CH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:20]([O:22][CH2:23][CH3:24])=[CH2:21].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>N1C=CC=CC=1.C(Cl)Cl>[C:1]1([CH:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]([O:11][CH:20]([O:22][CH2:23][CH3:24])[CH3:21])[CH:9]=[CH2:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 8023Ethyl vinyl etherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10467933HCID 10467933, compound

Product 1

HCID 15934455HCID 15934455, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

526 mg (2.0 mmol) of 1-phenyl-1-t-butoxycarbonylamino-2-hydroxybut-3-ene, syn form, 20 cm3 of dry methylene chloride, 1.9 cm3 (20.0 mmol) of distilled ethyl vinyl ether and 50.2 mg (0.2 mmol) of pyridinium p-toluenesulphonate (PPTS) are introduced successively into a 50 cm3 single-necked flask placed under an argon atmosphere and equipped with a magnetic stirring system. The resulting homogeneous reaction mixture is left to react for 4.5 hours at a temperature of about 20° C. When the reaction is complete, 1 drop of pyridine is added and the reaction mixture is then diluted in 60 cm3 of methylene chloride. The organic phase is washed twice with water and twice with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulphate. After filtration, the solvents are driven off under reduced pressure on a rotary evaporator. The residue obtained is purified by passage over a column of silica gel using a hexane/ether mixture (8/2 by volume) as the eluent. 580 mg (1.73 mmol) of 1-phenyl-1-t-butoxycarbonylamino-2-(1-ethoxyethoxy)but-3-ene are obtained with a yield of 87% in the form of two epimers in a ratio of 55/45, said product having the following characteristics:

Workup

  1. customequipped with a magnetic stirring system
  2. waitThe resulting homogeneous reaction mixture is left
  3. customto react for 4.5 hours at a temperature of about 20° C
  4. washThe organic phase is washed twice with water and twice with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationAfter filtration
  7. customthe solvents are driven off under reduced pressure on a rotary evaporator
  8. customThe residue obtained
  9. customis purified by passage over a column of silica gel using a hexane/ether mixture (8/2 by volume) as the eluent

Sources & evidence

ORD record
ord-7482d4dff34347018b1a3e0f11be3b73
Source dataset
uspto-grants-1994_03
Patent number
US05290957

Reaction notes

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