2,3-Dihydrofuran → HCID 70388777, compound

HRID 1193481Notes

Reaction equation

HRID 1193481 reaction equation
Cl.[Cl:2][C:3]1[C:4]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[O:17]1[CH:21]=[CH:20][CH2:19][CH2:18]1>O.C1COCC1>[Cl:2][C:3]1[C:4]([O:11][CH2:12][C:13]([F:15])([F:14])[F:16])=[C:5]([NH:9][N:10]=[CH:21][CH2:20][CH2:19][CH2:18][OH:17])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 709342,3-DihydrofuranHCID 21272039HCID 21272039, compound

Product 1

HCID 70388777HCID 70388777, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 3-chloro-2-(2,2,2-trifluoroethoxy)phenylhydrazine hydrochloride (13.3 g, 48 mmol) was dissolved in H2O (133 mL) and THF (133 mL). Dihydrofuran (3.75 mL, 48 mmol) was added in one portion, and the reaction mixture was stirred for 3 hours. After this time, the organic layer was separated and the aqueous layer extracted with Et2O (250 mL). The combined organic layers were washed with brine (250 mL), dried (MgSO4), and concentrated to afford 14 g (98%) of a 3:1 mixture of E:Z isomers of 4-[3-chloro-2-(2,2,2-trifluoroethoxy)phenylhydrazono]-1-butanol as an orange oil which was used without further purification.

Workup

  1. customAfter this time, the organic layer was separated
  2. extractionthe aqueous layer extracted with Et2O (250 mL)
  3. washThe combined organic layers were washed with brine (250 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto afford
  7. addition14 g (98%) of a 3:1 mixture of E
  8. customZ isomers of 4-[3-chloro-2-(2,2,2-trifluoroethoxy)phenylhydrazono]-1-butanol as an orange oil which was used without further purification

Sources & evidence

ORD record
ord-78ccaf18a00d4e608cae6046fb085c8f
Source dataset
uspto-grants-1989_03
Patent number
US04810699

Reaction notes

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