Triethylamine → (+/-)-3-Dimethylcarbamoylpropyl 2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate

HRID 2419929Notes

Reaction equation

HRID 2419929 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]([CH3:21])([C:17]([F:20])([F:19])[F:18])[C:14](Cl)=[O:15].[OH:22][CH2:23][CH2:24][CH2:25][C:26]([N:28]([CH3:30])[CH3:29])=[O:27].C(N(CC)CC)C>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]([CH3:21])([C:17]([F:20])([F:19])[F:18])[C:14]([O:22][CH2:23][CH2:24][CH2:25][C:26](=[O:27])[N:28]([CH3:30])[CH3:29])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130008164-hydroxy-N,N-dimethylbutanamideHCID 20314457(+/-)-2-(2-Naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionyl chloride

Product 1

HCID 20314445(+/-)-3-Dimethylcarbamoylpropyl 2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionateYield 34.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (±)-2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionyl chloride (3.0 g.) in tetrahydrofuran (70 ml.) is added, dropwise at 0° C., to a stirred solution of 4-hydroxy-N,N-dimethylbutyramide (1.20 g.) and triethylamine (2.1 g.) in tetrahydrofuran (35 ml.). The mixture is stored for 2 days. The solid is filtered off and washed with ether, and the filtrate and washings are evaporated. The residue is dissolved in ether and the solution is washed with water, 0.4 N aqueous sodium hydroxide, and water, dried with magnesium sulphate, and evaporated. The residue is crystallised from a mixture of light petroleum (b.p. 40°-60° C.) and ether to give (±)-3-dimethylcarbamoylpropyl 2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate (1.3 g.) m.p. 42°-43° C.

Workup

  1. filtrationThe solid is filtered off
  2. washwashed with ether
  3. customthe filtrate and washings are evaporated
  4. dissolutionThe residue is dissolved in ether
  5. washthe solution is washed with water, 0.4 N aqueous sodium hydroxide, and water
  6. dry with materialdried with magnesium sulphate
  7. customevaporated
  8. customThe residue is crystallised from a mixture of light petroleum (b.p. 40°-60° C.) and ether

Sources & evidence

ORD record
ord-7f558e373343479f9677b96ec66f0555
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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