Water → tert-Butyl (2-hydroxyethyl)(prop-2-yn-1-yl)carbamate

HRID 1971673Notes

Reaction equation

HRID 1971673 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH2:19][C:20]#[CH:21])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[OH:8][CH2:9][CH2:10][N:11]([CH2:19][C:20]#[CH:21])[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 11324466tert-Butyl (2-((tert-butyldimethylsilyl)oxy)ethyl)(prop-2-yn-1-yl)carbamate

Product 1

HCID 11672867tert-Butyl (2-hydroxyethyl)(prop-2-yn-1-yl)carbamateYield 115.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 950 mg of 10c in 5 ml of THF was added 5 ml of 1M tetra-n-butyl ammonium fluoride in THF. The mixture was stirred for 1 hr at RT and then poured into 50 ml of water and extracted with ethyl acetate. The crude product thus obtained was chromatographed on silica gel (using a gradient of heptane/ethyl acetateas eluent) and provided 700 mg of 10d, as a colorless oil; Rf 0.35 (heptane/ethyl acetate 1/1);

Workup

  1. extractionextracted with ethyl acetate
  2. customThe crude product thus obtained
  3. customwas chromatographed on silica gel (

Sources & evidence

ORD record
ord-bf9bb8e58aad41f9bb4a9d040233a80b
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…