Diethyl Ether → HCID 85668919, compound

HRID 54737Notes

Reaction equation

HRID 54737 reaction equation
[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4]([Cl:6])=[O:5].[CH2:10]([N:12](CC)CC)[CH3:11].CC[O:19]CC>O>[ClH:6].[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4]([O:19][CH2:11][CH2:10][NH2:12])=[O:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 109207893,4,4-Trifluoro-3-butenoyl chloride

Product 1

HCID 85668919HCID 85668919, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3,4,4-trifluoro-3-butenoyl chloride (1.97 g, 0.0124 mole) and N-t-Boc-aminoethanol (1.61 g, 0.010 mole) in dry ether (20 mL) is treated with triethylamine (1.25 g, 0.0124 mole) at -78° C. with stirring. The mixture is stirred for 30 min and allowed to reach room temperature and poured in 20 mL of water. The ether layer is successively washed with 5% sodium bicarbonate and brine and dried. The ether solution is saturated with dry HCl gas and stirred at room temperature for 30 min. The precipitate is filtered and dried to give 1.6 g of the title compound as a white solid, a 77% yield. m.p. 94°-100° C.

Workup

  1. stirringThe mixture is stirred for 30 min
  2. customto reach room temperature
  3. washThe ether layer is successively washed with 5% sodium bicarbonate and brine
  4. customdried
  5. stirringstirred at room temperature for 30 min
  6. filtrationThe precipitate is filtered
  7. customdried

Sources & evidence

ORD record
ord-ae228c421e374ea3882f43765a65a3c1
Source dataset
uspto-grants-1997_04
Patent number
US05623084

Reaction notes

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