Tetrahydrofuran → 2-[(3-Ethynylphenyl)amino]ethanol

HRID 1403189Notes

Reaction equation

HRID 1403189 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[CH:19])[CH:13]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>>[C:18]([C:14]1[CH:13]=[C:12]([NH:11][CH2:10][CH2:9][OH:8])[CH:17]=[CH:16][CH:15]=1)#[CH:19]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 89397433HCID 89397433, compound

Product 1

HCID 285642192-[(3-Ethynylphenyl)amino]ethanol

Procedure

N-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-3-ethynylaniline (335 mg, 1.22 mmol) was treated with 1M TBAF in THF (1.5 mL, 1.5 mmol) at room temperature for 5 min. The volatiles were removed and the crude was dissolved in EtOAc (30 mL). The organic phase was washed with water (20 mL) and finally with brine, dried over sodium sulfate and evaporated to give the corresponding alcohol as brownish oil.

Workup

  1. customThe volatiles were removed
  2. dissolutionthe crude was dissolved in EtOAc (30 mL)
  3. washThe organic phase was washed with water (20 mL) and finally with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-873eefa3c19a485e8db91fe06883c83a
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…