4-Chlorophenol → HCID 19983625, compound

HRID 1460280Notes

Reaction equation

HRID 1460280 reaction equation
[CH3:1][C:2]([CH3:8])([C:6]#[CH:7])[CH2:3][CH2:4][OH:5].[Cl:9][C:10]1[CH:15]=[CH:14][C:13](O)=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([O:5][CH2:4][CH2:3][C:2]([CH3:8])([CH3:1])[C:6]#[CH:7])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 102407894-Pentyn-1-ol, 3,3-dimethyl-

Product 1

HCID 19983625HCID 19983625, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.0 g (44.6 mmol) of 3,3-dimethyl-4-pentyn-1-ol and 5.7 g (44.6 mmol) of 4-chlorophenol in 125 ml of tetrahydrofuran cooled to 0° C. is added 11.7 g (44.6 mmol) of triphenyl phosphine followed by 7.8 g (7.0 ml, 44.6 mmol) of diethyl azodicarboxylate. The reaction mixture is allowed to warm to room temperature and stirred overnight. The solvent is evaporated and the residue triturated with hexane. The solid is filtered, washed with hexane and the resulting filtrate evaporated. The residue is subjected to flash chromatography (silica gel) using hexane as eluting solvent to afford 5.0 g of colorless crystalline solid: m.p. 42°-45° C.; NMR (CDCl3) δ1.3 (6H, s), 1.9 (2H, t, J=6.5 Hz), 2.12 (1H, s), 4.15 (2H, t, J=6.6 Hz), 6.8 (2H, d, J=9.0 Hz), 7.2 (2H, d, J=9.0 Hz).

Workup

  1. customThe solvent is evaporated
  2. customthe residue triturated with hexane
  3. filtrationThe solid is filtered
  4. washwashed with hexane
  5. customthe resulting filtrate evaporated
  6. washas eluting solvent

Sources & evidence

ORD record
ord-f4991a6f08934c5bac3e56edd0315bd5
Source dataset
uspto-grants-1991_12
Patent number
US05070207

Reaction notes

Loading…