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

HRID 2380126ノート

反応式

HRID 2380126 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

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.

後処理

  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),

出典と根拠

ORDレコード
ord-32b15fcea1fe45b9bbb8a75eac85eb43
出典データセット
uspto-grants-1994_11
特許番号
US05364844

反応ノート

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