Benzyl Alcohol → Benzyl 2(S)-benzyl-4-pentenoate

HRID 2380126Notes

Reaction equation

HRID 2380126 reaction equation
C([Li])CCC.[CH2:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:14]([C@@H:21]([CH2:33][CH:34]=[CH2:35])[C:22](N1[C@@H](C(C)C)COC1=O)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:14]([C@H:21]([CH2:33][CH:34]=[CH2:35])[C:22]([O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 25517Ammonium ChlorideHCID 186566433-[2(R)-benzyl-4-pentenoyl]-4(S)-isopropyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 14989078Benzyl 2(S)-benzyl-4-pentenoateYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

5.63 ml (9.01 mmoles) of butyllithium (as a 1.6M hexane solution) were added, whilst ice-cooling and under an atmosphere of nitrogen, to a solution of 1.24 ml (12.0 mmoles) of benzyl alcohol in 20 ml of anhydrous tetrahydrofuran. The mixture was stirred for 10 minutes, and then a solution of 1.81 g (6.01 mmoles) of 3-[2(R)-benzyl-4-pentenoyl]-4(S)-isopropyl-2-oxazolidinone (prepared by a procedure similar to that described in Preparation 17) in 10 ml of anhydrous tetrahydrofuran was added dropwise thereto. The mixture was then stirred for 30 minutes, after which a saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 10:1 by volume mixture of hexane and ethyl acetate as eluent), to give 1.58 g (yield 94%) of the title compound as a colorless oily substance.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was then stirred for 30 minutes
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customthe residue was purified by medium pressure silica gel column chromatography (
  7. additionby volume mixture of hexane and ethyl acetate as eluent),

Sources & evidence

ORD record
ord-32b15fcea1fe45b9bbb8a75eac85eb43
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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