(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehyde → 1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol

HRID 546373ノート

反応式

HRID 546373 の反応式
[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]=[O:12])([CH3:3])[CH3:2].[CH2:13]([Mg]Br)[C:14]#[CH:15]>C1COCC1>[CH:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([CH3:10])[CH2:6][C@H:5]1[CH:11]([OH:12])[CH2:15][C:14]#[CH:13])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 11252239(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexane-1-carbaldehydeHCID 178455849HCID 178455849、化合物2 回

生成物 1

HCID 866439371-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)but-3-yn-1-ol収率 37.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbaldehyde (1.0 g, 6.0 mmol) in THF (10 mL) at 0° C. was slowly added propargyl magnesium bromide (1 M, 8.9 mmol). After the reaction was allowed to warm to room temperature overnight 1.5 equivalents of additional propargyl magnesium bromide were added and the reaction was allowed to stir for 6 additional h. The reaction was again cooled to 0° C. and then quenched with 1 N HCl and partitioned between brine and MTBE. The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica chromatography to give the desired alcohol (0.47 g).

後処理

  1. customat 0° C.
  2. additionwere added
  3. customquenched with 1 N HCl
  4. custompartitioned between brine and MTBE
  5. dry with materialThe organic layer was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica chromatography

出典と根拠

ORDレコード
ord-345f706e4ffc4137be4f291a604843b2
出典データセット
uspto-grants-2011_05
特許番号
US07935848B2

反応ノート

読み込み中…