Hexane → HCID 87829549, compound

HRID 969251Notes

Reaction equation

HRID 969251 reaction equation
[Li]CCCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH3:12][C:13]1[N:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]([CH3:20])=[C:16]([PH2:19])[C:17]=1[PH2:18].[CH3:27][C@H:28](O)[CH2:29][CH2:30][C@@H:31](O)[CH3:32]>C1COCC1>[CH3:12][C:13]1[N:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]([CH3:20])=[C:16]([P:19]2[C@H:31]([CH3:32])[CH2:30][CH2:29][C@H:28]2[CH3:27])[C:17]=1[P:18]1[CH:10]([CH3:11])[CH2:9][CH2:8][CH:7]1[CH3:6]

Participants

6

Reactant 4

HCID 8058HexaneHCID 69502882,5-Hexanediol, (2S,5S)-HCID 59017167HCID 59017167, compoundHCID 178418339Butyllithium

Product 1

HCID 87829549HCID 87829549, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of BuLi 1.6M in hexane (0.96 mL, 1.53 mmol) was dropped in a solution of 2,5-dimethyl-3,4bis-(phosphino)1-phenyl-pyrrole prepared as described in the previous stage (180 mg, 0.77 mmol) in THF (14.4 mL) and the reaction mixture was left under stirring for 1.5 h. 233 mg (1.53 mmol) of the cyclic sulfate of (2S,5S) hexanediol dissolved in 1.2 mL of THF were dropped in the reaction mixture, which was subsequently left under stirring for 1 h. The reaction mixture was quenched with methanol (0.3 mL) and the solvent evaporated under reduced pressure. The solid was then washed with n-heptane (3×20 mL) and the solvent was removed from the filtrate by evaporation under reduced pressure (20 torr), thereby obtaining the desired product (133 mg, yield 44%).

Workup

  1. customprepared
  2. waitthe reaction mixture was left
  3. additionwere dropped in the reaction mixture, which
  4. waitwas subsequently left
  5. stirringunder stirring for 1 h
  6. customThe reaction mixture was quenched with methanol (0.3 mL)
  7. customthe solvent evaporated under reduced pressure
  8. washThe solid was then washed with n-heptane (3×20 mL)
  9. customthe solvent was removed from the filtrate by evaporation under reduced pressure (20 torr)

Sources & evidence

ORD record
ord-add182ed81584b3d8f36c37d2ad2260d
Source dataset
uspto-grants-2007_12
Patent number
US07307037B2

Reaction notes

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