Trifluoroacetic acid → HCID 11687874, compound

HRID 853167Notes

Reaction equation

HRID 853167 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1.[N-:19]=[C:20]=[O:21].[K+].FC(F)(F)C(O)=O>C1C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][O:15][C:20](=[O:21])[NH2:19])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11051572Potassio isocyanateHCID 69039049HCID 69039049, compound

Product 1

HCID 11687874HCID 11687874, compoundYield 44.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Under an argon atmosphere and at room temperature, a suspension of 1.0 g of 2-[4-(3-fluoro-benzyloxy)-phenyl]-ethanol and 0.66 g of potassium isocyanate in 2 ml of benzene was treated dropwise under stirring with 0.62 ml of trifluoroacetic acid. After stirring for 18 h at room temperature, the reaction mixture was diluted with water, then extracted three times with dichloromethane. The combined organic layers were dried over potassium carbonate and evaporated. There were obtained 0.52 g (44% of theory) of carbamic acid 2-[4-(3-fluoro-benzyloxy)-phenyl]-ethyl ester as a white solid; MS: m/e=290 (M+H)+.

Workup

  1. additionwas treated dropwise
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic layers were dried over potassium carbonate
  4. customevaporated

Sources & evidence

ORD record
ord-709065a3f569419ab1cc3846d37a282e
Source dataset
uspto-grants-2007_08
Patent number
US07253318B2

Reaction notes

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