Benzyl Alcohol → HCID 14964493, compound

HRID 1079025Notes

Reaction equation

HRID 1079025 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CC(C1COC(=O)N1[C:23](=[O:29])[CH:24]([CH3:28])[CH2:25][CH:26]=[CH2:27])C>O1CCCC1.CCCCCC.[Cl-].[NH4+].C(Cl)Cl>[C:2]1([CH2:1][O:8][C:23](=[O:29])[C@@H:24]([CH3:28])[CH2:25][CH:26]=[CH2:27])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 244Benzyl AlcoholHCID 12892386HCID 12892386, compoundHCID 178418339Butyllithium

Product 1

HCID 14964493HCID 14964493, compound

Reagents, catalysts & solvents 4

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 5.1 g of benzyl alcohol in 50 ml of tetrahydrofuran is added, dropwise, 3.8 ml of 2.5M n-butyl lithium in hexane. To this mixture is added, via cannula, a solution of 3.5 g of S-(R*,R*)]4-(1-methylethyl)-3-(2-methyl-1-oxo-4-pentenyl)-2-oxazolidinone in 100 ml of tetrahydrofuran. The resulting solution is stirred at 0° C. for 2 hours. The reaction is diluted with saturated aqueous ammonium chloride and methylene chloride. The organic layer is washed with water, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel, methylene chloride) to give 2.9 g of the desired product as a colorless oil. [α]D26 =+3° (methylene chloride).

Workup

  1. additionTo this mixture is added, via cannula
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-421f0c02cfb249e4be926fb250bc811e
Source dataset
uspto-grants-1996_08
Patent number
US05550257

Reaction notes

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