Propargyl alcohol → HCID 19843629, compound

HRID 2352672Notes

Reaction equation

HRID 2352672 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].C([Li])CCC.CCCCCC.[CH2:16]([S:24]C#N)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>O1CCCC1.CN(P(N(C)C)(N(C)C)=O)C>[CH2:16]([S:24][C:3]#[C:2][CH2:1][OH:4])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

7

Reactant 4

HCID 7859Propargyl alcoholHCID 8058HexaneHCID 29864Octyl thiocyanateHCID 178418339Butyllithium

Product 1

HCID 19843629HCID 19843629, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

To a solution of 2-propynol (0.65 g/0.68 ml, 11.7 mmol) in 25 ml of tetrahydrofuran (THF), cooled to -60°, is slowly added butyllithium in hexane (14.6 ml, 23.3 mmol) over 5 min. About 5 ml of HMPA is added and the mixture is warmed to -20° and stirred for 5 min. The mixture is then cooled again to -60° and octylthiocyanate (2.0 g, 11.7 mmol) in 3 ml of THF is added over 1 min. The mixture is allowed to warm to RT over 1 hour and is stirred at RT for an additional hour. It is then cooled to -10° and quenched with water. The reaction mixture is diluted with ether, washed with water and brine and dried to give 3-octylthio-2-propynol.

Workup

  1. customover 5 min
  2. temperaturethe mixture is warmed to -20°
  3. temperatureThe mixture is then cooled again to -60°
  4. stirringis stirred at RT for an additional hour
  5. temperatureIt is then cooled to -10°
  6. customquenched with water
  7. additionThe reaction mixture is diluted with ether
  8. washwashed with water and brine
  9. customdried

Sources & evidence

ORD record
ord-3492ae7c57d548d2b6eaa3535438ba6a
Source dataset
uspto-grants-1989_10
Patent number
US04877899

Reaction notes

Loading…